Synthesis, Self-assembly and Photophysical Properties of A Three-state Highly Emissive Mesogen

ZHENG Jun-feng; GONG Jia-xin; CHENG Xiao-fan; GE Yun-chong; XU Peng

doi:10.37188/CJL.20220047

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Synthesis, Self-assembly and Photophysical Properties of A Three-state Highly Emissive Mesogen

Synthesis and Properties of Materials | 更新时间：2022-10-19

- Synthesis, Self-assembly and Photophysical Properties of A Three-state Highly Emissive Mesogen
  增强出版
- Chinese Journal of Luminescence Vol. 43, Issue 6, Pages: 869-878(2022)
- 作者机构：
  
  南京林业大学化学工程学院应用化学系，江苏南京　210037
- 作者简介：
- 基金信息：
- DOI：10.37188/CJL.20220047
  CLC： O753⁺.2
- Published：05 June 2022，
  
  Received：15 February 2022，
  
  Revised：02 March 2022，
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郑军峰,宫佳鑫,程晓帆等.一种三态发光的液晶基元合成、自组装及光物理性质[J].发光学报,2022,43(06):869-878.

ZHENG Jun-feng,GONG Jia-xin,CHENG Xiao-fan,et al.Synthesis, Self-assembly and Photophysical Properties of A Three-state Highly Emissive Mesogen[J].Chinese Journal of Luminescence,2022,43(06):869-878.
郑军峰,宫佳鑫,程晓帆等.一种三态发光的液晶基元合成、自组装及光物理性质[J].发光学报,2022,43(06):869-878. DOI： 10.37188/CJL.20220047.

ZHENG Jun-feng,GONG Jia-xin,CHENG Xiao-fan,et al.Synthesis, Self-assembly and Photophysical Properties of A Three-state Highly Emissive Mesogen[J].Chinese Journal of Luminescence,2022,43(06):869-878. DOI： 10.37188/CJL.20220047.

摘要

聚集导致猝灭（ACQ）分子在单分子态（如稀溶液）高效发光，而聚集诱导发光（AIE）分子在聚集态（如固态）高效发光。这一单态发光的特性严重制约着发光材料的应用。本工作中，我们合成了一种三态（溶液、凝胶、液晶）发光的phasmid液晶基元（

PHAgen-12

），并考察了其自组装性质与光物理性质。

PHAgen-12

的两端为一代树枝单元，中间为“二苯基氰基乙烯（AIE）+二苯基丁二炔（ACQ）+二苯基氰基乙烯（AIE）”的刚性核，具有D-A-π-A-D的特征。该分子在普通溶剂（如THF、DCM）中可以溶解；在选择性溶剂烷烃中形成柱状胶束，并可凝胶化；在固态形成六方柱状液晶相，单分子层厚度（～0.44 nm）的单胞内含有～4个分子。

PHAgen-12

在单分子态表现出ACQ分子的性质，在氯仿中荧光量子产率（QY）为～90.3%；在聚集态表现出AIE性质，

PHAgen-12

/十二烷凝胶体系（质量百分比为30%）的QY为58.5%，本体液晶态的QY为85.5%。

Abstract

Aggregation-caused quenching（ACQ） and aggregation-induced emission（AIE） molecules are highly emissive only in single molecular and aggregated state， respectively. This single-state emissive character highly hampers their applications. In this work， we synthesized a three-state（solution， gel and liquid crystal） highly emissive phasmid mesogen（

PHAgen-12

） and studied its self-assembly and photophysical properties.

PHAgen-12

consists of a long rod-like part ended by two Percec-type dendrons. The rod-like core is “cyanostilbene + diphenyl-diacetylene+cyanostilbene”， featuring a D-A-π-A-D type emitter.

PHAgen-12

can well dissolve in common solvents such as THF and DCM， form cylindrical micelle and further gel in selective solvents（alkanes）， and develop into a hexagonal columnar liquid crystalline phase in bulk state， with four molecules in each monomolecule-thick（～0.44 nm） hexagonal unit cell. In dilute solution， it behaves like a ACQ molecule with a quantum yield（QY） up to 90.3 % in CHCl

. It renders a strong AIE character in condensed states， with a QY of 58.5% in

PHAgen-12/

dodecane gel system（30%（wt）） and a QY of 85.5% in bulk liquid crystalline state

关键词

多态发光液晶凝胶聚集诱导发光（AIE）聚集导致荧光猝灭（ACQ）

Keywords

multi-state emissiveliquid crystalgelaggregation-induced emission（AIE）aggregation-caused quenching（ACQ）

references

XU S D，DUAN Y K，LIU B. Precise molecular design for high-performance luminogens with aggregation-induced emission ［J］. Adv. Mater.， 2020，32（1）：1903530-1-31. doi: 10.1002/adma.201903530http://dx.doi.org/10.1002/adma.201903530

MEI J，LEUNG N L C，KWOK R T K，et al. Aggregation-induced emission：together we shine，united we soar！［J］. Chem. Rev.， 2015，115（21）：11718-11940. doi: 10.1021/acs.chemrev.5b00263http://dx.doi.org/10.1021/acs.chemrev.5b00263

FENG G X，LIU B. Aggregation-induced emission（AIE） dots：emerging theranostic nanolights ［J］. Acc. Chem. Res.， 2018，51（6）：1404-1414. doi: 10.1021/acs.accounts.8b00060http://dx.doi.org/10.1021/acs.accounts.8b00060

WANG Y J，NIE J Y，FANG W，et al. Sugar-based aggregation-induced emission luminogens：design，structures，and applications ［J］. Chem. Rev.， 2020，120（10）：4534-4577. doi: 10.1021/acs.chemrev.9b00814http://dx.doi.org/10.1021/acs.chemrev.9b00814

ZHELEV Z，OHBA H，BAKALOVA R. Single quantum dot-micelles coated with silica shell as potentially non-cytotoxic fluorescent cell tracers ［J］. J. Am. Chem. Soc.， 2006，128（19）：6324-6325. doi: 10.1021/ja061137dhttp://dx.doi.org/10.1021/ja061137d

BAKALOVA R，ZHELEV Z，AOKI I，et al. Silica-shelled single quantum dot micelles as imaging probes with dual or multimodality ［J］. Anal. Chem.， 2006，78（16）：5925-5932. doi: 10.1021/ac060412bhttp://dx.doi.org/10.1021/ac060412b

LUO J D，XIE Z L，LAM J W Y，et al. Aggregation-induced emission of 1-methyl-1，2，3，4，5-pentaphenylsilole ［J］. Chem. Commun.， 2001（18）：1740-1741. doi: 10.1039/b105159hhttp://dx.doi.org/10.1039/b105159h

CHEN G，LI W B，ZHOU T R，et al. Conjugation-induced rigidity in twisting molecules：filling the gap between aggregation-caused quenching and aggregation-induced emission ［J］. Adv. Mater.， 2015，27（30）：4496-4501. doi: 10.1002/adma.201501981http://dx.doi.org/10.1002/adma.201501981

LI M，NIU Y L，ZHU X Z，et al. Tetrahydro［5］helicene-based imide dyes with intense fluorescence in both solution and solid state ［J］. Chem. Commun.， 2014，50（23）：2993-2995. doi: 10.1039/c3cc49680ehttp://dx.doi.org/10.1039/c3cc49680e

WU H W，CHEN Z，CHI W J，et al. Structural engineering of luminogens with high emission efficiency both in solution and in the solid state ［J］. Angew. Chem. Int. Ed.， 2019，58（33）：11419-11423. doi: 10.1002/anie.201906507http://dx.doi.org/10.1002/anie.201906507

ZHAO Z J，CHEN S M，LAM J W Y，et al. Creation of highly efficient solid emitter by decorating pyrene core with AIE-active tetraphenylethene peripheries ［J］. Chem. Commun.， 2010，46（13）：2221-2223. doi: 10.1039/b921451hhttp://dx.doi.org/10.1039/b921451h

SHIH P I，CHUANG C Y，CHIEN C H，et al. Highly efficient non-doped blue-light-emitting diodes based on an anthrancene derivative end-capped with tetraphenylethylene groups ［J］. Adv. Funct. Mater.， 2007，17（16）：3141-3146. doi: 10.1002/adfm.200700355http://dx.doi.org/10.1002/adfm.200700355

YUAN W Z，LU P，CHEN S M，et al. Changing the behavior of chromophores from aggregation-caused quenching to aggregation-induced emission：development of highly efficient light emitters in the solid state ［J］. Adv. Mater.， 2010，22（19）：2159-2163. doi: 10.1002/adma.200904056http://dx.doi.org/10.1002/adma.200904056

BISOYI H K，LI Q. Liquid crystals：versatile self-organized smart soft materials ［J］. Chem. Rev.， 2022，122（5）：4887-4926. doi: 10.1021/acs.chemrev.1c00761http://dx.doi.org/10.1021/acs.chemrev.1c00761

WÖHRLE T，WURZBACH I，KIRRES J，et al. Discotic liquid crystals ［J］. Chem. Rev.， 2016，116（3）：1139-1241. doi: 10.1021/acs.chemrev.5b00190http://dx.doi.org/10.1021/acs.chemrev.5b00190

CHEN X F，SHEN Z H，WAN X H，et al. Mesogen-jacketed liquid crystalline polymers ［J］. Chem. Soc. Rev.， 2010，39（8）：3072-3101. doi: 10.1039/b814540ghttp://dx.doi.org/10.1039/b814540g

NGUYEN H T，DESTRADE C，MALTHÉCTE J. Phasmids and polycatenar mesogens ［J］. Adv. Mater.，1997，9（5）：375-388. doi: 10.1002/adma.19970090503http://dx.doi.org/10.1002/adma.19970090503

GHARBIA M，GHARBI A，NGUYEN H T，et al. Polycatenar liquid crystals with long rigid aromatic cores：a review of recent works ［J］. Curr. Opin. Colloid Interface Sci.， 2002，7（5-6）：312-325. doi: 10.1016/s1359-0294(02)00087-0http://dx.doi.org/10.1016/s1359-0294(02)00087-0

王嘉慧，曾晓璇，吴玥，等. 具有pH响应性能的聚集诱导发光材料制备与表征［J］. 发光学报， 2021，42（3）：311-318. doi: 10.37188/CJL.20210020http://dx.doi.org/10.37188/CJL.20210020

WANG J H，ZENG X X，WU Y，et al. Synthesis and characterization of pH-responsive material with aggregation-induced emission property ［J］. Chin. J. Lumin.， 2021，42（3）：311-318. （in Chinese）. doi: 10.37188/CJL.20210020http://dx.doi.org/10.37188/CJL.20210020

陆红波，吴少君，张超，等. α-氰基取代二苯乙烯衍生物的合成与发光特性研究［J］. 发光学报，2015，36（9）：983-988. doi: 10.3788/fgxb20153609.0983http://dx.doi.org/10.3788/fgxb20153609.0983

LU H B，WU S J，ZHANG C，et al. Synthesis and photoluminescence property of α-cyanostilbene derivatives molecules ［J］. Chin. J. Lumin.， 2015，36（9）：983-988. （in Chinese）. doi: 10.3788/fgxb20153609.0983http://dx.doi.org/10.3788/fgxb20153609.0983

白向阳，陈诺，檀文，等. 席夫碱修饰的α-氰基二苯乙烯荧光液晶材料的合成与发光性质［J］. 发光学报， 2016，37（5）：532-537. doi: 10.3788/fgxb20163705.0532http://dx.doi.org/10.3788/fgxb20163705.0532

BAI X Y，CHEN N，TAN W，et al. Synthesis and luminescence property of Schiff base modified α-cyanostilbene derivative fluorescent liquid crystals material ［J］. Chin. J. Lumin.， 2016，37（5）：532-537. （in Chinese）. doi: 10.3788/fgxb20163705.0532http://dx.doi.org/10.3788/fgxb20163705.0532

MENG Z G，FU K，ZHAO Y，et al. Aggregation-induced red-shifted emission and fluorescent patterning of poly（aryleneethynylene） with a lateral AIEgen substituent ［J］. J. Mater. Chem. C， 2020，8（3）：1010-1016. doi: 10.1039/c9tc05854khttp://dx.doi.org/10.1039/c9tc05854k

ZHENG J F，TANG T，DING L L，et al. Phase behavior of phasmidic mesogen-jacketed liquid crystalline polymers displaying chain bundling ［J］. Macromolecules，2019，52（14）：5389-5398. doi: 10.1021/acs.macromol.9b00687http://dx.doi.org/10.1021/acs.macromol.9b00687

ZONG L Y，XIE Y J，WANG C，et al. From ACQ to AIE：the suppression of the strong π-π interaction of naphthalene diimide derivatives through the adjustment of their flexible chains ［J］. Chem. Commun.， 2016，52（77）：11496-11499. doi: 10.1039/c6cc06176ahttp://dx.doi.org/10.1039/c6cc06176a

LU H G，ZHENG Y D，ZHAO X W，et al. Highly efficient far red/near-infrared solid fluorophores：aggregation-induced emission，intramolecular charge transfer，twisted molecular conformation，and bioimaging applications ［J］. Angew. Chem. Int. Ed.， 2016，55（1）：155-159. doi: 10.1002/anie.201507031http://dx.doi.org/10.1002/anie.201507031

郑军峰(1983-)，男，河南平舆人，博士，讲师，2012年于北京大学获得博士学位，主要从事高分子合成、自组装与功能的研究。. doi: 10.1002/anie.201507031http://dx.doi.org/10.1002/anie.201507031

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Department of Chemistry, Key Laboratory of Functional Inorganic Materials of Anhui Province, Anhui University, Hefei 230601, China

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