ZHENG Junfeng,CHENG Xiaofan,GE Yunchong,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,2023,44(05):863-872.
ZHENG Junfeng,CHENG Xiaofan,GE Yunchong,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,2023,44(05):863-872. DOI: 10.37188/CJL.20220428.
Synthesis, Phase Structure and Photophysical Property of A Liquid Crystalline Molecule with High Emission Efficiency both in Solution and Solid State增强出版
Organic luminogens can be divided roughly into two main classes: aggregation-caused quenching (ACQ) and aggregation-induced emission (AIE) molecules, which are highly emissive only in single molecular and aggregated state, respectively. In this work, we synthesized a liquid crystalline molecule (
MS⁃12
) with high emission efficiency both in solution and solid state and studied its liquid crystalline and photophysical properties.
MS⁃12
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. It shows 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.
LU H B, ZHANG C, WU S J, et al. Synthesis and photoluminescence property of luminescent liquid crystal material [J]. Chin. J. Lumin., 2015, 36(11): 1227-1232. (in Chinese). doi: 10.3788/fgxb20153611.1227http://dx.doi.org/10.3788/fgxb20153611.1227
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
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
FRIEND R H, GYMER R W, HOLMES A B, et al. Electroluminescence in conjugated polymers [J]. Nature, 1999, 397(6715): 121-128. doi: 10.1038/16393http://dx.doi.org/10.1038/16393
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): 1419-11423. doi: 10.1002/anie.201906507http://dx.doi.org/10.1002/anie.201906507
DALAPATI S, JIN E Q, ADDICOAT M, et al. Highly emissive covalent organic frameworks [J]. J. Am. Chem. Soc., 2016, 138(18): 5797-5800. doi: 10.1021/jacs.6b02700http://dx.doi.org/10.1021/jacs.6b02700
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
HONG Y N, LAM J W Y, TANG B Z. Aggregation-induced emission: phenomenon, mechanism and applications [J]. Chem. Commun., 2009, (29): 4332-4353. doi: 10.1039/b904665hhttp://dx.doi.org/10.1039/b904665h
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
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
YUAN W Z, YU Z Q, TANG Y H, et al. High solid-state efficiency fluorescent main chain liquid crystalline polytriazoles with aggregation-induced emission characteristics [J]. Macromolecules, 2011, 44(24): 9618-9628. doi: 10.1021/ma2021979http://dx.doi.org/10.1021/ma2021979
ZHAO Q L, ZHANG S, LIU Y, et al. Tetraphenylethenyl-modified perylene bisimide: aggregation-induced red emission, electrochemical properties and ordered microstructures [J]. J. Mater. Chem., 2012, 22(15): 7387-7394. doi: 10.1039/c2jm16613ehttp://dx.doi.org/10.1039/c2jm16613e
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
ZHANG Y F, WANG Y C, YU X S, et al. Isophthalate-based room temperature phosphorescence: from small molecule to side-chain jacketed liquid crystalline polymer [J]. Macromolecules, 2019, 52(6): 2495-2503. doi: 10.1021/acs.macromol.9b00171http://dx.doi.org/10.1021/acs.macromol.9b00171
ZHENG J F, GONG J X, CHENG X F, et al. Synthesis, self-assembly and photophysical properties of a three-state highly emissive mesogen [J]. Chin. J. Lumin., 2022, 43(6): 869-878. (in Chinese). doi: 10.37188/CJL.20220047http://dx.doi.org/10.37188/CJL.20220047
CUI L Y, SONG Z Y, ZHAO X Y, et al. Fabrication and optical property of diacetylene derivative [J]. Chin. J. Lumin., 2016, 37(12): 1491-1495. (in Chinese). doi: 10.3788/fgxb20163712.1491http://dx.doi.org/10.3788/fgxb20163712.1491
JUN T, PARK H, JEON S, et al. Mesoscale frank-kasper crystal structures from dendron assembly by controlling core apex interactions [J]. J. Am. Chem. Soc., 2021, 143(42): 17548-17556. doi: 10.1021/jacs.1c07313http://dx.doi.org/10.1021/jacs.1c07313
DIROLL B T, JISHKARIANI D, CARGNELLO M, et al. Polycatenar ligand control of the synthesis and self-assembly of colloidal nanocrystals [J]. J. Am. Chem. Soc., 2016, 138(33): 10508-10515. doi: 10.1021/jacs.6b04979http://dx.doi.org/10.1021/jacs.6b04979
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
LEE W W H, ZHAO Z, CAI Y J, et al. Facile access to deep red/near-infrared emissive AIEgens for efficient non-doped OLEDs [J]. Chem. Sci., 2018, 9(28): 6118-6125. doi: 10.1039/c8sc01377bhttp://dx.doi.org/10.1039/c8sc01377b
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