Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State

Zheng Jun-feng; Cheng Xiao-fan; Ge Yun-chong; Gong Jia-xin; Xu Peng

doi:10.37188/CJL.20220428

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Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State

Updated：2023-02-03

- Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State Enhanced Publication
- Chinese Journal of Luminescence Vol.null, Issue null, (2023)
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  Department of Applied Chemistry， College of Chemical Engineering， Nanjing Forestry University,Nanjing,China,210037
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- DOI：10.37188/CJL.20220428 CLC：
- Published Online：03 February 2023，
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郑军峰,程晓帆,葛云翀等.固液双态高效发光的液晶分子的合成、相结构及光物理性质[J].发光学报,

Zheng Jun-feng,Cheng Xiao-fan,Ge Yun-chong,et al.Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State[J].Chinese Journal of Luminescence,
郑军峰,程晓帆,葛云翀等.固液双态高效发光的液晶分子的合成、相结构及光物理性质[J].发光学报, DOI：10.37188/CJL.20220428

Zheng Jun-feng,Cheng Xiao-fan,Ge Yun-chong,et al.Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State[J].Chinese Journal of Luminescence, DOI：10.37188/CJL.20220428

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In this work， we synthesized a liquid crystalline molecule （" }, { "name": "bold", "data": [ { "name": "text", "data": "MS-12" } ] }, { "name": "text", "data": "） with high emission efficiency both in solution and solid state and studied its liquid crystalline and photophysical properties." }, { "name": "bold", "data": [ { "name": "text", "data": "MS-12 " } ] }, { "name": "text", "data": "consists of a long rod-like core ended by two Percec-type dendrons. The rigid core is composed of cyanostilbene and diphenylacetylene units， featuring a D-A-π-A-D emitter. It renders a hexagonal columnar liquid crystalline phase in bulk state， with four molecules in each monomolecular-thick （～0.44 nm） hexagonal unit cell. In dilute solution， it behaves like a ACQ molecule with a quantum yield （QY） up to 78.1%in THF.Itshows a strong AIE character in condensed state， with a QY of 59.6% in bulk liquid crystalline state. This work provides a general strategy to multi-state emissive organic luminogens， those in particular with liquid crystalline properties." } ] } ] } ], "keyword": [ { "lang": "zh", "data": [ [ { "name": "text", "data": "聚集诱导发光（AIE）" } ], [ { "name": "text", "data": "聚集导致荧光淬灭（ACQ）" } ], [ { "name": "text", "data": "多态发光" } ], [ { "name": "text", "data": "液晶" } ] ] }, { "lang": "en", "data": [ [ { "name": "text", "data": "aggregation-induced emission （AIE）" } ], [ { "name": "text", "data": "aggregation-caused quenching （ACQ）" } ], [ { "name": "text", "data": "multi-state emissive" } ], [ { "name": "text", "data": "liquid crystal" } ] ] } ], "highlights": [], "body": [ { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "1　引言" } ], "level": "1", "id": "s1" } }, { "name": "p", "data": [ { "name": "text", "data": "多功能材料克服了功能单一的缺点，在现代科学与技术领域有重要的应用。例如，兼具发光与液晶的材料在各向异性发光二极管、信息存储、传感器、半导体等领域具有广泛应用" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "blockXref", "data": { "data": [ { "name": "xref", "data": { "text": "1", "type": "bibr", "rid": "R1", "data": [ { "name": "text", "data": "1" } ] } }, { "name": "text", "data": "-" }, { "name": "xref", "data": { "text": "4", "type": "bibr", "rid": "R4", "data": [ { "name": "text", "data": "4" } ] } } ], "rid": [ "R1", "R2", "R3", "R4" ], "text": "1-4", "type": "bibr" } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。可以想象，多功能材料设计的一个直观的方法是把多种单一功能的分子砌块通过合理的分子设计整合到一个分子中，使其发挥各个砌块的功能，以最终得到多功能材料。然而，在多数情况下这种方案并非有效，其原因是不同功能的实现往往遵循不同的分子机理，要求不同的分子形状与分子排列，以致不同的功能之间难以协同，常常相互抵消或减弱" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "5", "type": "bibr", "rid": "R5", "data": [ { "name": "text", "data": "5" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。因而，如何通过合理的分子设计把不同功能的砌块整合到一个分子中使其有效发挥各个砌块的功能具有重要的科学和实践意义。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "有机发光分子主要有聚集导致淬灭（aggregation-caused quenching, ACQ）和聚集诱导发光（aggregation-induced emission, AIE）分子，其发光机理并不相同" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "blockXref", "data": { "data": [ { "name": "xref", "data": { "text": "6", "type": "bibr", "rid": "R6", "data": [ { "name": "text", "data": "6" } ] } }, { "name": "text", "data": "-" }, { "name": "xref", "data": { "text": "7", "type": "bibr", "rid": "R7", "data": [ { "name": "text", "data": "7" } ] } } ], "rid": [ "R6", "R7" ], "text": "6-7", "type": "bibr" } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。典型的ACQ分子砌块如苝四酰亚胺、二苯基丁二炔、苯炔苯等" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "8", "type": "bibr", "rid": "R8", "data": [ { "name": "text", "data": "8" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。ACQ分子为高度共轭的共平面结构，在稀溶液态，平面构象能有效抑制分子内运动（基团的振动和转动），抑制非辐射跃迁，因而其发光能力强；而在聚集态，共轭平面间因π-π相互作用而密堆积，促进激子相互作用，导致荧光淬灭" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "5", "type": "bibr", "rid": "R5", "data": [ { "name": "text", "data": "5" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。因此，ACQ分子在稀溶液态发光能力强，而在聚集态发光减弱甚至不发光。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "典型的AIE分子砌块如四苯基乙烯、氰基二苯乙烯等" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "9", "type": "bibr", "rid": "R9", "data": [ { "name": "text", "data": "9" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。在这些分子中，取代基可绕C―C单键内旋转，因而采取三维形状。例如，四苯基乙烯为螺旋桨状构象，氰基二苯乙烯为扭曲的构象。在稀溶液态，AIE分子的分子内运动比较自由，因而非辐射跃迁较大；而在聚集态，空间位阻有效抑制了分子内运动，抑制了非辐射跃迁。因此，AIE分子在稀溶液态不发光，而在聚集态发光" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "blockXref", "data": { "data": [ { "name": "xref", "data": { "text": "10", "type": "bibr", "rid": "R10", "data": [ { "name": "text", "data": "10" } ] } }, { "name": "text", "data": "-" }, { "name": "xref", "data": { "text": "11", "type": "bibr", "rid": "R11", "data": [ { "name": "text", "data": "11" } ] } } ], "rid": [ "R10", "R11" ], "text": "10-11", "type": "bibr" } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "由上述可知，ACQ分子仅仅在稀溶液态高效发光，AIE分子仅仅在聚集态高效发光。于是，我们提出一个问题：能否通过把ACQ与AIE砌块直接相连（即ACQ+AIE策略）制备在稀溶液态和聚集态都能高效发光的有机发光分子呢？实验表明，ACQ+AIE分子通常在单分态不发光，而在聚集态高效发光" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "blockXref", "data": { "data": [ { "name": "xref", "data": { "text": "12", "type": "bibr", "rid": "R12", "data": [ { "name": "text", "data": "12" } ] } }, { "name": "text", "data": "-" }, { "name": "xref", "data": { "text": "14", "type": "bibr", "rid": "R14", "data": [ { "name": "text", "data": "14" } ] } } ], "rid": [ "R12", "R13", "R14" ], "text": "12-14", "type": "bibr" } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。其原因是：在稀溶液态，AIE单元的分子内运动使ACQ+AIE分子内非辐射跃迁增加，因而ACQ+AIE溶液发光效率低" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "15", "type": "bibr", "rid": "R15", "data": [ { "name": "text", "data": "15" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "；而在聚集态，AIE单元的三维形状能有效抑制ACQ单元间的π-π密堆积，减少非辐射跃迁，因而ACQ+AIE固态发光效率高" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "16", "type": "bibr", "rid": "R16", "data": [ { "name": "text", "data": "16" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。因此，如能有效提高ACQ+AIE在单分态的共轭程度，ACQ+AIE策略将是制备固液双态发光有机分子的有效策略。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "分子内电荷转移效应是提高分子共轭程度、共面性的有效方法" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "12", "type": "bibr", "rid": "R12", "data": [ { "name": "text", "data": "12" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。因此，如在ACQ+AIE单元中引入电子给体（D）和电子受体（A）单元，提高ACQ+AIE的分子内电荷转移能力，将有效提高ACQ+AIE单元的共轭性、共面性，减少其分子内运动，减少其非辐射跃迁，因而提高ACQ+AIE单元在单分态的发光效率，解决ACQ+AIE单元在稀溶液态发光效率低的问题，有望得到在稀溶液态和聚集态都能高效发光的有机材料。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "最近，Y. L. Zhao 和朱亮亮课题组合作证实了上述设想，作者通过在ACQ+AIE中引入D-A结构，得到了在晶态、无定形态、稀溶液中均能高效发光的有机分子（如" }, { "name": "xref", "data": { "text": "图1", "type": "fig", "rid": "F1", "data": [ { "name": "text", "data": "图1" } ] } }, { "name": "text", "data": "a所示）" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "8", "type": "bibr", "rid": "R8", "data": [ { "name": "text", "data": "8" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。但作者合成的有机分子是结晶小分子，晶体材料的加工性差，不适合大面积加工。而液晶材料兼具晶体的部分有序性和液体的流动性，适合大面积加工，是制备功能材料的理想平台" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "17", "type": "bibr", "rid": "R17", "data": [ { "name": "text", "data": "17" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。因此，把ACQ+AIE多态发光材料的分子设计概念引入到液晶分子的设计中具有重要科学和实践意义。在前期的研究中，我们以二苯基丁二炔为ACQ单元，氰基二苯乙烯为AIE单元，合成了多态发光的液晶分子（如" }, { "name": "xref", "data": { "text": "图1", "type": "fig", "rid": "F1", "data": [ { "name": "text", "data": "图1" } ] } }, { "name": "text", "data": "b所示）" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "18", "type": "bibr", "rid": "R18", "data": [ { "name": "text", "data": "18" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。然而，丁二炔单元热稳定性差、在光照下易聚合" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "19", "type": "bibr", "rid": "R19", "data": [ { "name": "text", "data": "19" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "、合成较为困难，这些缺点限制了其合成、光物理性质表征以及应用。考虑到二苯基丁二炔单元的这些缺点，本工作中，我们选择更易合成、更稳定的苯炔苯作为ACQ单元，设计了目标分子MS-12（如" }, { "name": "xref", "data": { "text": "图1", "type": "fig", "rid": "F1", "data": [ { "name": "text", "data": "图1" } ] } }, { "name": "text", "data": "c所示），并对其化学结构、凝聚态结构以及光物理性质进行了充分的表征。研究表明，MS-12在本体态能形成六方柱状液晶相，在稀溶液中和本体液晶态均能高效发光，并具有优异的加工性和热稳定性。" } ] }, { "name": "fig", "data": { "id": "F1", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图1" } ], "title": [ { "name": "text", "data": "本工作及相关研究的化学结构" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.1" } ], "title": [ { "name": "text", "data": "Chemical structures of MS-12 and its related molecules reported previously" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481241&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481243&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481242&type=", "width": "123.82499695", "height": "65.28199768", "fontsize": "" } ] } } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "2　实　　验" } ], "level": "1", "id": "s2" } }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "2.1　试剂与仪器" } ], "level": "2", "id": "s2a" } }, { "name": "p", "data": [ { "name": "text", "data": "1-溴十二烷、没食子酸甲酯、四丁基溴化铵（TBAB）、4-炔基苯甲醛、1,4-二碘苯、四（三苯基膦钯）（Pd(PPh" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": ")" }, { "name": "sub", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "）购自毕得医药；正十二烷（C" }, { "name": "sub", "data": [ { "name": "text", "data": "12" } ] }, { "name": "text", "data": "H" }, { "name": "sub", "data": [ { "name": "text", "data": "26" } ] }, { "name": "text", "data": "）、二氯亚砜（SOCl" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "）、氘代氯仿（CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "）、氢化铝锂（LiAlH" }, { "name": "sub", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "）、碘化亚铜（CuI）购自安耐吉化学；二氯甲烷（DCM）、四氢呋喃（THF）、N,N-二甲基甲酰胺（DMF）、甲醇、乙醇（EtOH）、叔丁醇（t-BuOH）、三乙胺（Et" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "N）、石油醚等溶剂购自探索平台；氯仿（CHCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "）、丙酮、甲苯（Toluene）、浓盐酸（HCl）、1,2-二氯乙烷、金属钠（Na）购自南京化学试剂有限公司；碳酸钾（K" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "CO" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "）、氢氧化钾（KOH）、氯化钠（NaCl）、硫酸钠（Na" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "SO" }, { "name": "sub", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "）购自国药集团化学试剂有限公司。THF在Na存在下、在氮气保护下回流4 h后蒸出，其它原料未经进一步纯化直接使用。" } ] }, { "name": "p", "data": [ { "name": "sup", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "H NMR和" }, { "name": "sup", "data": [ { "name": "text", "data": "13" } ] }, { "name": "text", "data": "C NMR采用Bruker 的AVANCE III HD 400MHz 核磁共振仪进行检测，溶剂为CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "，内标为四甲基硅烷(TMS)。样品的元素分析采用PerkinElmer 2400II进行测量。一维X-射线衍射（1D XRD）采用仪器X’Pert Pro (Philips)进行测试。示差扫描量热（DSC）分析采用德国Netzsch DSC-200F3 Maia进行测量；偏光显微（POM）分析采用Nikon ECLIPSELV100NPOL，其附有热台INSTEC HCS 400。样品的紫外-可见吸收光谱采用PerkinElmer Lambda 950型紫外-可见分光光度计进行测量；样品的荧光发射谱仪采用 PerkinElmer FL 6500荧光光谱仪进行测量;样品的荧光量子产率采用爱丁堡-稳态/瞬态荧光光谱仪FLS 1000进行测量。" } ] } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "2.2　合成方法" } ], "level": "2", "id": "s2b" } }, { "name": "p", "data": [ { "name": "text", "data": "目标分子的合成路线如下" }, { "name": "xref", "data": { "text": "图2", "type": "fig", "rid": "F2", "data": [ { "name": "text", "data": "图2" } ] } }, { "name": "text", "data": "所示：" } ] }, { "name": "fig", "data": { "id": "F2", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图2" } ], "title": [ { "name": "text", "data": "目标phasmidic液晶基元MS-12的合成路线" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.2" } ], "title": [ { "name": "text", "data": "Synthetic route to MS-12" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481244&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481246&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481245&type=", "width": "138.85299683", "height": "90.11453247", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "中间体1的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "参照文献报道的方法合成" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "20", "type": "bibr", "rid": "R20", "data": [ { "name": "text", "data": "20" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。在500 mL圆底烧瓶中加入7.37 g（40 mmol）3,4,5-三羟基苯甲酸甲酯，31.92 g（128 mmol）1-溴十二烷，11.04 g（80 mmol）K" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "CO" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "，200 mL丙酮，和催化量的四丁基溴化铵，在氮气保护下回流直至TLC分析表明3,4,5-三羟基苯甲酸甲酯反应完全。最终得到22.1 g白色粉末状固体（产率80%），即中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "，其核磁氢谱如图S1所示。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体2的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "参照文献报道的方法合成" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "20", "type": "bibr", "rid": "R20", "data": [ { "name": "text", "data": "20" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。往250 mL圆底烧瓶中加入20.00 g（29 mmol）中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "，再加入100 mL干燥的THF，在冰浴条件下搅拌10 min，然后缓慢加入1.21g（31.9 mmol）四氢铝锂并继续搅拌30 min。将反应转移至油浴中，氮气保护下回流至TLC分析表明M1反应完全。最终得到16.4 g白色块状固体（产率85%），即中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "，直接用于下一步反应。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体3的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "参照文献报道的方法合成" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "21", "type": "bibr", "rid": "R21", "data": [ { "name": "text", "data": "21" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。往250 mL单口圆底烧瓶中加入15 g（22.69 mmol）中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "，再加入85 mL DCM，室温搅拌15 min，然后缓慢滴入2.28 mL（3.74 g，31.76 mmol）SOCl" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "，再滴入两滴DMF，于氮气保护下低温搅拌4 h；经TLC分析表明中间体2反应完全。最终得到14 g白色粉末状固体（产率90.8%），即中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "3，" } ] }, { "name": "text", "data": "其核磁氢谱如图S2所示。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体4的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "往250 mL单口圆底烧瓶中加入10 g（14.71 mmol）中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "，再加入2 g（17.68 mmol）4-羟基苯乙腈、8.1 g（58.60 mmol）无水碳酸钾、催化量的TBAB和100 mL丙酮，在回流状态下搅拌直至TLC分析表明中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "反应完全。将体系中的无机盐过滤除去，再将通过旋转蒸发仪将丙酮除去得到粗产物；将粗产物用DCM溶解后与适量硅胶粉混合，通过旋转蒸发仪除去DCM，直至得到松散的粉末；粉末再通过干法上样柱层析分离（洗脱剂为DCM），得到9.7 g白色粉末状固体（产率84.9%），即中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "，其核磁氢谱如图S3所示。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "中间体5的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "向100 mL双口瓶中加入1.5 g（4.6 mmol）1,4-二碘苯、1.3 g（10mmol）4-炔基苯甲醛、30 mL干燥的THF和10 mL 的Et" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "N。在N" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "氛围下加入催化量的Pd(PPh" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": ")" }, { "name": "sub", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "和CuI，80°C下继续搅拌过夜后停止反应。通过旋转蒸发仪除去反应液，剩余物经DCM萃取、饱和NaCl水溶液洗涤、无水Na" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "SO" }, { "name": "sub", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "干燥后，用1,2-二氯乙烷重结晶两次，最终得到0.79 g淡黄色粉末状固体（产率52.00%），即为中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "5" } ] }, { "name": "text", "data": "，其核磁氢谱如图S4所示。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "目标分子的合成：" } ] }, { "name": "p", "data": [ { "name": "text", "data": "在100 mL单口圆底烧瓶中依次加入2.2 g（2.83 mmol）中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "4" } ] }, { "name": "text", "data": "、0.4 g（1.20 mmol）中间体" }, { "name": "bold", "data": [ { "name": "text", "data": "5" } ] }, { "name": "text", "data": "、0.26 g（4.63 mmol）KOH、42 mL 的THF和14 mL的 t-BuOH，55 °C下搅拌12 h后停止反应。向反应瓶中加入适量硅胶，通过旋转蒸发仪除去反应液，直至得到松散的粉末；粉末通过干法上样柱层析分离（洗脱剂为DCM和石油醚）得到 1.26 g黄色粉末状固体（产率 57.00%）目标化合物" }, { "name": "bold", "data": [ { "name": "text", "data": "MS-12" } ] }, { "name": "text", "data": "，其核磁氢谱如" }, { "name": "xref", "data": { "text": "图3", "type": "fig", "rid": "F3", "data": [ { "name": "text", "data": "图3" } ] } }, { "name": "text", "data": "所示，其核磁碳谱如图S5所示。" } ] }, { "name": "fig", "data": { "id": "F3", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图3" } ], "title": [ { "name": "text", "data": "目标phasmidic液晶基元MS-12在CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "中的" }, { "name": "sup", "data": [ { "name": "text", "data": "1 " } ] }, { "name": "text", "data": "H NMR" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.3" } ], "title": [ { "name": "sup", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "H NMR spectrum of MS-12 in CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481247&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481249&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481248&type=", "width": "117.61599731", "height": "90.02899933", "fontsize": "" } ] } } ] } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "3　结果与讨论" } ], "level": "1", "id": "s3" } }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "3.1　目标分子MS-12的化学结构确认" } ], "level": "2", "id": "s3a" } }, { "name": "p", "data": [ { "name": "text", "data": "目标分子MS-12的" }, { "name": "sup", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "H NMR如" }, { "name": "xref", "data": { "text": "图3", "type": "fig", "rid": "F3", "data": [ { "name": "text", "data": "图3" } ] } }, { "name": "text", "data": "所示。烷基链上的H位于（0. 5～5. 5）ppm之间，共154H，苯环的H和双键的H位于（7. 2～8）ppm之间，共26H，这与化学结构相符。" }, { "name": "sup", "data": [ { "name": "text", "data": "1" } ] }, { "name": "text", "data": "H NMR (400 MHz, CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3 " } ] }, { "name": "text", "data": ", 298 K) δ (ppm) : 7.89 (t, 4H, Ar-H), 7.71 – 7.60 (m, 8H, Ar-H), 7.57 (d, 4H, Ar-H), 7.44 (s, 2H, CH), 7.07 (d, 4H, Ar-H), 6.65 (s, 4H, Ar-H), 5.03 (s, 4H, OCH" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "), 3.99 (dd, 12H, OCH" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "), 1.81 (t, 12H, CH" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "), 1.49 (s, 12H, CH" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "), 1.31 (d, 96H, CH" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "), 0.91 (t, 18H, CH" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": ")." }, { "name": "sup", "data": [ { "name": "text", "data": "13" } ] }, { "name": "text", "data": "C NMR (100 MHz, CDCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3 " } ] }, { "name": "text", "data": ", 298 K) δ (ppm) : 159.84 , 153.41 , 138.96 , 138.16 , 133.86 , 132.06 , 131.72 , 131.29 , 129.08 , 127.42 , 127.08 , 124.77 , 123.09 , 118.02 , 115.43 , 111.75 , 106.17 , 91.51 , 91.17 , 73.47 , 70.62 , 69.20 , 31.96 , 29.90 – 29.22 , 26.16 , 22.73 , 14.15 . Anal. calcd for C" }, { "name": "sub", "data": [ { "name": "text", "data": "126" } ] }, { "name": "text", "data": "H" }, { "name": "sub", "data": [ { "name": "text", "data": "180" } ] }, { "name": "text", "data": "N" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O" }, { "name": "sub", "data": [ { "name": "text", "data": "8" } ] }, { "name": "text", "data": ": C, 81.77; H, 9.80; N, 1.51; Found: C, 81.79; H, 9.75; N, 1.51." } ] } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "3.2　目标分子MS-12的本体液晶性质" } ], "level": "2", "id": "s3b" } }, { "name": "p", "data": [ { "name": "text", "data": "为考察MS-12的相转变行为，我们首先对MS-12进行了DSC分析。以20 °C/min的速率加热到200 °C，然后进行等温退火5min以消除热历史，再以速率为10 °C/min进行降温，采集第一次降温和第二次升温的实验数据（如" }, { "name": "xref", "data": { "text": "图4", "type": "fig", "rid": "F4", "data": [ { "name": "text", "data": "图4" } ] } }, { "name": "text", "data": "所示）。从" }, { "name": "xref", "data": { "text": "图4", "type": "fig", "rid": "F4", "data": [ { "name": "text", "data": "图4" } ] } }, { "name": "text", "data": "中可知，在第一次降温过程中，在106和138 °C处分别出现两个放热峰；第二次升温过程中，在117和144°C/min处分别出现两个吸热峰。这两个转变峰的过冷度小，表明其很有可能对应于液晶相转变，而非结晶相转变。" } ] }, { "name": "fig", "data": { "id": "F4", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图4" } ], "title": [ { "name": "text", "data": "目标分子MS-12的DSC曲线，升降温速率为10 °C/min" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.4" } ], "title": [ { "name": "text", "data": "DSC traces of MS-12 recorded during the first cooling and second heating at a rate of 10 °C/min" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481250&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481252&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481251&type=", "width": "77.69583130", "height": "61.28518677", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "接着我们又通过POM来观察MS-12的双折射性质，降温过程中在～140 °C以下MS-12具有明显的双折射性质，呈现典型的扇形织构，并且随温度变化扇形织构变化不大，这意味着在各向同性温度以下，MS-12可能形成柱状液晶相。" } ] }, { "name": "fig", "data": { "id": "F5", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图5" } ], "title": [ { "name": "text", "data": "化合物 MS-12从各向同性温度缓慢降至室温的 POM 图" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.5" } ], "title": [ { "name": "text", "data": "POM image of MS-12 recorded on cooling from its isotropic melt to room temperature" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481253&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481255&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481254&type=", "width": "55.26300049", "height": "45.15599823", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "为进一步确定MS-12的液晶相结构，我们对其进行了1D XRD分析。将MS-12加热至恰好熔融，待其冷却至室温后包于锡箔纸内，并在真空烘箱于90 °C下退火约12小时，采集样品室温下的衍射数据（如" }, { "name": "xref", "data": { "text": "图6", "type": "fig", "rid": "F6", "data": [ { "name": "text", "data": "图6" } ] } }, { "name": "text", "data": "所示）。" }, { "name": "xref", "data": { "text": "图6", "type": "fig", "rid": "F6", "data": [ { "name": "text", "data": "图6" } ] } }, { "name": "text", "data": "的衍射曲线在低角区出现三个尖锐的衍射峰，分别位于1.68°、2.76°和3.32°，其相对应的d值分别为5.3 nm，3.2 nm，2.7 nm，其比值为1：" }, { "name": "inlineformula", "data": [ { "name": "math", "data": { "math": "

1 / \sqrt[]{3}

", "graphicsData": { "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481257&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481256&type=", "width": "8.89000034", "height": "4.31799984", "fontsize": "" } } } ] }, { "name": "text", "data": "：1/2。这表明MS-12在室温下形成了六方柱状液晶相，三个衍射峰可依次指标化为（100）、（110）和（200）。广角区较为弥散的衍射包集中在～20°，对应的d值为～0.44 nm，这意味着在柱状相中，MS-12单分子层的厚度约为0.44 nm。通过悬浮法测得的样品密度ρ=0.95 g/cm" }, { "name": "sup", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "，根据公式" }, { "name": "inlineformula", "data": [ { "name": "math", "data": { "math": "

μ = (s h) ρ (N A / M)

", "graphicsData": { "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481259&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481258&type=", "width": "27.34733391", "height": "3.64066648", "fontsize": "" } } } ] }, { "name": "text", "data": "可以计算单分子厚度的单胞内含有的分子平均个数μ= 4.41，其中单胞面积" }, { "name": "inlineformula", "data": [ { "name": "math", "data": { "math": "

s = 2 d_{100}^{2} / \sqrt[]{3}

", "graphicsData": { "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481261&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481260&type=", "width": "20.15066719", "height": "4.65666676", "fontsize": "" } } } ] }, { "name": "text", "data": "，M为MS-12的分子量（M = 1850.83 g / mol），N" }, { "name": "sub", "data": [ { "name": "text", "data": "A" } ] }, { "name": "text", "data": "为阿伏伽德罗常数，h为单个分子层在沿着柱轴方向所占的平均厚度（～0.44 nm，如" }, { "name": "xref", "data": { "text": "图7", "type": "fig", "rid": "F7", "data": [ { "name": "text", "data": "图7" } ] } }, { "name": "text", "data": "所示）。基于XRD分析，我们提出了MS-12在柱状液晶相中的分子排列模型（如" }, { "name": "xref", "data": { "text": "图7", "type": "fig", "rid": "F7", "data": [ { "name": "text", "data": "图7" } ] } }, { "name": "text", "data": "所示）。四个分子以近平行的方式形成四聚体，四聚体以螺旋的形式形成超分子柱，进而形成六方柱状液晶相" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "22", "type": "bibr", "rid": "R22", "data": [ { "name": "text", "data": "22" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。" } ] }, { "name": "fig", "data": { "id": "F6", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图6" } ], "title": [ { "name": "text", "data": "化合物MS-12从各向同性温度缓慢降至室温的1D XRD图" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.6" } ], "title": [ { "name": "text", "data": "1D XRD profile of powder sample of MS-12 upon slowly cooling from 140 ℃ to room temperature" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481262&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481264&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481263&type=", "width": "77.69583130", "height": "61.08795166", "fontsize": "" } ] } }, { "name": "fig", "data": { "id": "F7", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图7" } ], "title": [ { "name": "text", "data": "化合物MS-12在六方柱状液晶相中的分子排列模型图" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.7" } ], "title": [ { "name": "text", "data": "Schematic of the molecular packing model of MS-12 in hexagonal columnar liquid crystalline phase" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481265&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481267&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481266&type=", "width": "119.01000214", "height": "51.62900162", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "以上POM、DSC、1D XRD的分析结果表明，MS-12在从室温到～110 °C的温度区间形成六方柱状液晶相，在110～140 °C的温度区间可能也为柱状液晶相，但超分子柱排列的对称性需要变温XRD进一步确认。" } ] } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "3.3　目标产物的光物理性质" } ], "level": "2", "id": "s3c" } }, { "name": "p", "data": [ { "name": "text", "data": "我们对MS-12在稀溶液态和聚集态的光物理性质进行了详细的表征。MS-12在C" }, { "name": "sub", "data": [ { "name": "text", "data": "12" } ] }, { "name": "text", "data": "H" }, { "name": "sub", "data": [ { "name": "text", "data": "26" } ] }, { "name": "text", "data": "、Toluene、CHCl" }, { "name": "sub", "data": [ { "name": "text", "data": "3" } ] }, { "name": "text", "data": "、THF和DMF溶解后的（溶剂极性依次增加）紫外-可见吸收光谱如" }, { "name": "xref", "data": { "text": "图8", "type": "fig", "rid": "F8", "data": [ { "name": "text", "data": "图8" } ] } }, { "name": "text", "data": "（a）所示。MS-12在五种溶液中均在385 nm附近出现最大吸收峰，这与体系中π–π*跃迁相对应。我们用同样的溶剂及浓度测试了MS-12的荧光发射谱，如" }, { "name": "xref", "data": { "text": "图8", "type": "fig", "rid": "F8", "data": [ { "name": "text", "data": "图8" } ] } }, { "name": "text", "data": "（b）所示。MS-12在C" }, { "name": "sub", "data": [ { "name": "text", "data": "12" } ] }, { "name": "text", "data": "H" }, { "name": "sub", "data": [ { "name": "text", "data": "26" } ] }, { "name": "text", "data": "中于426 nm附近出现了强而尖锐的峰，同时在447 nm附近还有一个强度稍弱、相对弥散的肩峰，二者分别对应于苯炔苯单元和氰基二苯乙烯发射基团" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "23", "type": "bibr", "rid": "R23", "data": [ { "name": "text", "data": "23" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。随着溶剂极性的增加，双峰发生了显著地红移，肩峰变得更加弥散且双峰有融合为一个峰的趋势，可以观察到在365 nm紫外照射下溶液从蓝紫色逐渐变为天蓝色，这表明分子在溶液中存在分子内电荷转移（intramolecular charge transfer, ICT）效应" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "blockXref", "data": { "data": [ { "name": "xref", "data": { "text": "23", "type": "bibr", "rid": "R23", "data": [ { "name": "text", "data": "23" } ] } }, { "name": "text", "data": "-" }, { "name": "xref", "data": { "text": "24", "type": "bibr", "rid": "R24", "data": [ { "name": "text", "data": "24" } ] } } ], "rid": [ "R23", "R24" ], "text": "23-24", "type": "bibr" } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。" } ] }, { "name": "fig", "data": { "id": "F8", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图8" } ], "title": [ { "name": "text", "data": "样品MS-12在不同溶剂中的紫外-可见吸收光谱（a）和荧光发射谱图（b）；MS-12在混合溶剂THF/H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O中的荧光发射谱图（c）；MS-12在混合溶剂中的相对荧光强度（I/I" }, { "name": "sub", "data": [ { "name": "text", "data": "0" } ] }, { "name": "text", "data": "）与" }, { "name": "italic", "data": [ { "name": "text", "data": "f" } ] }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] }, { "name": "text", "data": "（H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O）之间的关系图（d）" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.8" } ], "title": [ { "name": "text", "data": "Normalized absorbance spectra （a）and normalized emission spectra of compound MS-12 in different solvents upon 365 nm excitation （b）； Normalized emission spectra of MS-12 in THF/water mixtures （c）； Plot of the relative （I/I" }, { "name": "sub", "data": [ { "name": "text", "data": "0" } ] }, { "name": "text", "data": "） versus the " }, { "name": "italic", "data": [ { "name": "text", "data": "f" } ] }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] }, { "name": "text", "data": "（H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O） in mixed solvent of MS-12 （d）" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481268&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481270&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481269&type=", "width": "149.71899414", "height": "115.69300079", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "为了进一步探究稀溶液中的强发光现象，我们采用密度泛函理论（DFT）计算来研究MS-12的基态和激发态构象。" }, { "name": "xref", "data": { "text": "图9", "type": "fig", "rid": "F9", "data": [ { "name": "text", "data": "图9" } ] } }, { "name": "text", "data": "（a）为MS-12在激发态下最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）的电子分布。HOMO的电子云主要分布在芳香结构上，而LUMO的电子云除了分布在芳香结构之外，在氰基附近也有更集中的分布。HOMO和LUMO的显著差异证明了MS-12存在ICT效应。此外，MS-12的计算能隙为4.612eV，最大振子强度分别为3.3725，对应的最大吸收波长为384 nm，这与我们得到的紫外可见吸收光谱结果吻合。对比" }, { "name": "xref", "data": { "text": "图9", "type": "fig", "rid": "F9", "data": [ { "name": "text", "data": "图9" } ] } }, { "name": "text", "data": "（b）中基态与激发态的分子构象，苯基与氰基的二面角分别从11.5°减小到9°以及从12°减小到11°，这进一步表明了由于苯-炔-苯单元与氰基产生了ICT效应，从而促进分子在溶液中形成平面构象，有效降低氰基二苯乙烯非辐射能的消耗，提高了分子在溶液中的发光效率。" } ] }, { "name": "fig", "data": { "id": "F9", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图9" } ], "title": [ { "name": "text", "data": "MS-12的LUMO和HOMO分布（a）和MS-12在基态和激发态下的几何构象（b）" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.9" } ], "title": [ { "name": "text", "data": "HOMO and LUMO distribution of MS-12（a） and Geometrical conformation of MS-12 in ground and excited states（b）" } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481271&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481273&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481272&type=", "width": "112.94200134", "height": "64.71700287", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "为了探究MS-12在聚集态下的光物理性质，我们研究了MS-12在THF-H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O的混合溶液中不同H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O体积分数（" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "）中的发射行为，结果如图" }, { "name": "xref", "data": { "text": "8", "type": "fig", "rid": "F8", "data": [ { "name": "text", "data": "8" } ] } }, { "name": "text", "data": "（c）和" }, { "name": "xref", "data": { "text": "8", "type": "fig", "rid": "F8", "data": [ { "name": "text", "data": "8" } ] } }, { "name": "text", "data": "（d）所示。在纯THF溶剂中，MS-12发出强烈的深蓝色荧光，发射图谱上出现一个强而尖锐的峰和一个弱而弥散肩峰，分别为441 nm 和476 nm。" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "(H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O)在0%~40%时，溶液的荧光强度随着水含量的增大逐渐降低，这可能是扭曲分子内电荷转移（TICT）导致的" }, { "name": "sup", "data": [ { "name": "text", "data": "[" }, { "name": "xref", "data": { "text": "25", "type": "bibr", "rid": "R25", "data": [ { "name": "text", "data": "25" } ] } }, { "name": "text", "data": "]" } ] }, { "name": "text", "data": "。TICT是由供电子单元和接受电子单元构成的有机分子中常见的光物理现象。在极性环境中，分子内的电子迅速地从供体转移到受体，分子内D-A结构的构象从共面结构转变为扭曲构象，大部分能量以非辐射能的形式被耗散，导致荧光强度降低。由于氰基二苯乙烯是典型的D-A结构，该类分子往往具有TICT特性，而TICT效应和AIE效应是决定荧光强度的主要竞争因素。一方面，" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "(H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O) 在50% ~ 80%时，荧光强度开始随着水含量的增大而逐渐增加，" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "(H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O)在80%时的荧光发射强度较40%时增加了约1.5倍。由于水是MS-12的不良溶剂，故随着水体积分数的上升，氰基二苯乙烯基团逐渐开始聚集，这就迫使其由相对扭曲的构象逐渐转变为近平面化的构象，这种分子构象平面化有利于共轭长度的延长，同时使非辐射跃迁耗散减弱，因此疏水环境减轻了聚集体中的TICT效应，使AIE效应作为主导因素更为明显，从而导致溶液荧光强度增加。另一方面，随着水含量的增加，溶液的最大发射波长也出现了红移的现象。这是由于体系聚集程度的增加，导致分子之间的排列更加紧密，使体系中π–π共轭程度增强，从而导致最大发射波长出现红移。当" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "(H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O)在80% ~ 90%时，MS-12的荧光发光强度随水含量的增加而急剧降低。我们猜测随着过量水的加入使得聚集程度过大，出现了聚集体沉淀析出的现象，进而导致溶液中MS-12的实际浓度降低。综上，在" }, { "name": "italic", "data": [ { "name": "text", "data": "f" }, { "name": "sub", "data": [ { "name": "text", "data": "w" } ] } ] }, { "name": "text", "data": "(H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O)不断增加的过程中，荧光强度呈现先减弱后增强的现象，这说明了发光过程受到TICT效应和AIE效应的共同作用，证明了MS-12具有聚集诱导发光效应。" } ] }, { "name": "p", "data": [ { "name": "text", "data": "探究了MS-12在纯溶剂及THF-H" }, { "name": "sub", "data": [ { "name": "text", "data": "2" } ] }, { "name": "text", "data": "O混合溶液中的光物理性质后，我们又测试了其在本体态下的光物理性质。本体态MS-12在424 nm附近出现最大吸收峰,如" }, { "name": "xref", "data": { "text": "图10", "type": "fig", "rid": "F10", "data": [ { "name": "text", "data": "图10" } ] } }, { "name": "text", "data": "（a），在522 nm附近出现最大发射峰,如" }, { "name": "xref", "data": { "text": "图10", "type": "fig", "rid": "F10", "data": [ { "name": "text", "data": "图10" } ] } }, { "name": "text", "data": "（b）。最大发射峰与溶液中相比发生了显著红移，这是由于分子在固态呈现出较大程度的聚集，使得共轭程度增加所致。" } ] }, { "name": "fig", "data": { "id": "F10", "caption": [ { "lang": "zh", "label": [ { "name": "text", "data": "图10" } ], "title": [ { "name": "text", "data": "MS-12本体态的紫外-可见吸收光谱图（a）和荧光发射谱图（b）；插图：MS-12本体态在黑暗环境下使用365 nm紫外照射时拍摄的荧光照片" } ] }, { "lang": "en", "label": [ { "name": "text", "data": "Fig.10" } ], "title": [ { "name": "text", "data": "Absorbance spectra （a） and emission spectra of MS-12 as bulk liquid crystalline state （b）； Inset： Fluorescence photograph of MS-12 powders taken under 365 nm UV irradiation in the dark." } ] } ], "subcaption": [], "note": [], "graphics": [ { "print": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481274&type=", "small": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481276&type=", "big": "http://html.publish.founderss.cn/rc-pub/api/common/picture?pictureId=39481275&type=", "width": "126.68299866", "height": "51.92900085", "fontsize": "" } ] } }, { "name": "p", "data": [ { "name": "text", "data": "我们测定了MS-12分子在良溶剂稀的THF中的QY为～78.1%，固态QY为～59.6%。高的溶液发光效率应由ICT效应引起的分子共面性所致。高的固态发光效率也应与柱状液晶相的分子排列有关。1D XRD上没有呈现π-π相互作用所对应的特征衍射（0.38～0.40 nm）（" }, { "name": "xref", "data": { "text": "图6", "type": "fig", "rid": "F6", "data": [ { "name": "text", "data": "图6" } ] } }, { "name": "text", "data": "），表明在超分子柱中MS-12的排列较为松散（如" }, { "name": "xref", "data": { "text": "图7", "type": "fig", "rid": "F7", "data": [ { "name": "text", "data": "图7" } ] } }, { "name": "text", "data": "所示）。这种松散的分子排列可有效抑制分子密堆积导致的荧光淬灭效应，提高固态发光效率。实验结果表明，MS-12克服了ACQ分子和AIE分子的单态发光的缺点，是一类在单分子和聚集态都能高效发光的物质。" } ] } ] } ] }, { "name": "sec", "data": [ { "name": "sectitle", "data": { "title": [ { "name": "text", "data": "4　结　　论" } ], "level": "1", "id": "s4" } }, { "name": "p", "data": [ { "name": "text", "data": "本工作中，我们把多态发光分子的设计概念ACQ+AIE引入到phasmid型液晶分子中，合成了多态发光分子MS-12；其ACQ部分由苯炔苯单元构成，AIE部分由氰基苯乙烯单元构成；由于氰基的吸电子效应以及氧原子的供电子效应，具有D-A-π-A-D的结构特征，有效增加了单分态的共轭程度和共面性。通过NMR和元素分析对MS-12的化学结构进行了确认；通过DSC、POM、XRD对其液晶性质和分子排列进行了表征；通过紫外-可见吸收谱、荧光发射谱、密度泛函理论对其光物理性质进行了表征。研究表明，MS-12在本体态形成六方柱状液晶相，单分子厚度的单胞内含有～4个分子；分子内具有较强的分子内电荷转移效应，具有多态发光性质，在本体液晶态的荧光量子产率为～59.6%，在稀的THF中的荧光量子产率为～78.1%。本研究为多态发光液晶的设计提供了一个新的方向。" } ] } ] } ], "footnote": [], "reflist": { "title": [ { "name": "text", "data": "参考文献" } ], "data": [ { "id": "R1", "label": "1", "citation": [ { "lang": "en", "text": [ { "name": "text", "data": "Molard Y" }, { "name": "text", "data": " ， " }, { "name": "text", 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Synthesis, phase structure and photophysical property of a liquid crystalline molecule with high emission efficiency both in solution and solid State Enhanced Publication