调控有机小分子晶体力致发光行为的方法

doi:10.6023/A22050240

化学学报 ›› 2022, Vol. 80 ›› Issue (9): 1309-1321.DOI: 10.6023/A22050240 上一篇下一篇

综述

调控有机小分子晶体力致发光行为的方法

贾彦荣^a, 高贯雷^a, 夏敏^a^,^b^,^*()

a 浙江理工大学化学系杭州 310018
b 浙江理工大学生态染整技术教育部工程研究中心杭州 310018

投稿日期:2022-05-25 发布日期:2022-07-27
通讯作者: 夏敏

作者简介:

贾彦荣, 山东临沂人, 讲师, 2015年毕业于浙江理工大学, 获得理学博士学位. 主要从事有机荧光小分子的设计、合成及其在固液态下的性能研究.

高贯雷, 山东菏泽人, 2017年毕业于滨州学院, 获得工学学士学位, 目前在浙江理工大学化学系攻读理学硕士学位. 主要进行有机荧光小分子的合成及其固态发光性能的研究.

夏敏, 浙江余姚人, 教授, 1999年6月毕业于浙江大学有机化学专业, 获得理学博士学位. 目前任职于浙江理工大学生态染整技术教育部工程研究中心和理学院化学系, 博士生导师, 浙江省“151人才培养工程”入选人员, 浙江省中青年学术带头人. 主持国家级与省部级科研项目十余项, 发表SCI论文70余篇. 研究方向为有机小分子光电材料, 研究对象主要为有机共轭发光体系, 研究范围包括聚集诱导发光、多刺激响应荧光变色、摩擦发光、荧光探针与传感器等.

基金资助:
浙江省自然科学基金(LY19B020015)

Methods for Adjusting Mechanoluminescence Behaviors on Crystals of Purely Organic Small Molecules

Yanrong Jia^a, Guanlei Gao^a, Min Xia^a^,^b()

a Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, China
b Engineering Research Center for Eco-dyeing and Finishing Technology of Textiles, Ministry of Education, Zhejiang Sci-Tech University, Hangzhou 310018, China

Received:2022-05-25 Published:2022-07-27
Contact: Min Xia
Supported by:
Natural Science Fund of Zhejiang Province(LY19B020015)

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摘要/Abstract

尽管力致发光(mechanoluminescence, ML)现象的发现至今已有超过400年的历史, 但直到最近几十年才再次走入人们关注的视野. 这种与分子堆积关系密切的固体光学现象已经在光电材料领域内得到了一些应用, 并蕴藏着巨大的开发前景. 近年来, 随着有机功能化合物的蓬勃发展, 对力致发光材料的探索已逐渐从无机与高分子化合物、有机金属配合物、陶瓷等方面转到纯有机小分子晶体. 此外, 随着人们对有机小分子力致发光活性晶体认识的不断深入, 该领域的研究兴趣也从最初的如何获得此类晶体变为如何调控晶体的力致发光行为从而使其呈现出ML性能的差异. 本综述将对一些调控有机小分子晶体力致发光性能的手段, 例如物理方法、手性活化、分子结构改造、主客体掺杂、同质多晶形成等进行总结, 同时也将分子堆积与分子间相互作用对晶体发光性能的影响进行探讨, 并在此基础上对有机小分子力致发光晶体研究领域的未来发展提出建设性的展望.

关键词: 力致发光, 有机小分子晶体, 性能与调控方法

Although mechanoluminescence (ML) phenomenon has been discovered for more than 400 years, it has not gone into the research focus once again until recent decades. This type of solid-state optical effect which is heavily dependent on molecular packing has been applied in some optoelectrical materials and possesses large potentials in the future high-tech fields. Currently, as the researches on organic functional materials flourish, more and more attentions have been transferred from ML-active inorganic, polymeric, organometallic compounds and ceramics onto ML-active crystals of purely organic small molecules. Due to the gradually deepened understanding for ML-active crystals of purely organic small molecules, the research interests have shifted from how to obtain ML-active compounds onto how to design and develop molecules so that ML-active purely organic crystals with differentiated ML behaviors can be produced. In this review, some methods for generating distinct ML performances, including physical adjustment, chirality activation, structural modification, polymorph formation, host-guest doping and so on are summarized. Meanwhile, how molecular packing and intermolecular interactions make impacts on ML effect in individual systems are also discussed herein and some constructive outlook about the future progress in aspect of ML study is accordingly proposed.

Key words: mechanoluminescence, crystals of purely organic small molecules, performances and adjusting methods

引用此文

贾彦荣, 高贯雷, 夏敏. 调控有机小分子晶体力致发光行为的方法[J]. 化学学报, 2022, 80(9): 1309-1321.

Yanrong Jia, Guanlei Gao, Min Xia. Methods for Adjusting Mechanoluminescence Behaviors on Crystals of Purely Organic Small Molecules[J]. Acta Chimica Sinica, 2022, 80(9): 1309-1321.

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图/表 20

图1. CZEO晶体的ML谱图(插图: 紫外光照前后ML的出现与消失)(a); 分子间相互作用方式与光照前后分子间作用力的变化(b, c)[36]

Figure 1. ML spectrum of CZEO crystal (inserted: appearance and disappearance of ML effect before and after UV irradiation) (a); inter- molecular interactions and their strength change before and after UV irradiation) (b, c)[36]

图2. 热诱导转晶示意图(a); m-CN的结构式与两个同质多晶的ML照片(b); 两个同质多晶的荧光照片(c)与分子堆积(d)[37]

Figure 2. Schematic diagram of heat-induced crystalline transformation (a); structure of m-CN and photos of ML on two polymorphs (b); photos of two polymorphs under UV light (c) and molecular packing in them (d)[37]

图3. Cz-alkyl-6、NPC和Cz-Chol的结构式(a, c, e); Cz-alkyl-6、NPC和Cz-Chol的主客体掺杂物的ML照片(b, d, f)[38⇓-40]

Figure 3. Structures of Cz-alkyl-6, NPC and Cz-Chol (a, c, e); photos of ML for Cz-alkyl-6, NPC and Cz-Chol host-guest mixtures (b, d, f)[38⇓-40]

图4. 各种化合物同质多晶的分子结构(a, d, g, j, m, p)、ML活性晶体的发光照片(b, e, h, k, n, q)以及晶体中的分子堆积(c, f, i, l, o, r) [41⇓⇓⇓⇓-46]

Figure 4. Chemical structures of polymorphs (a, d, g, j, m, p), photos of ML-active crystals emission (b, e, h, k, n, q), molecular packing in each polymorphs (c, f, i, l, o, r)[41⇓⇓⇓⇓-46]

图5. CDpP的结构式(a)、两个同质多晶的ML发光照片(b)、ML谱图(c)、分子堆积(d)以及发射机理示意图(e)[47]

Figure 5. Structure of CDpP (a), photos of ML effect (b), ML spectra (c), molecular packing (d) and schematic diagram of ML mechanism (e) for the two polymorphs[47]

图6. TBIM的结构式(a)、两个同质多晶的ML谱图及发光照片(b)以及分子堆积(c)[48]

Figure 6. Structure of TBIM (a); ML spectra and photos (b) and molecular packing (c) for two polymorphs [48]

图7. (R)/(S)-ImNT的结构式(a); 对映异构体晶体与外消旋体晶体的荧光偏振光谱(b)与ML光谱(c)[49]

Figure 7. Structure of (R)/(S)-ImNT (a); CPL spectra (b) and ML spectra (c) of enantiomers and racemate crystals [49]

Figure 8. PI衍生物和PI-Ar衍生物的结构(a, d); PI-CF3, PI-T3与PI-N晶体的ML照片(b, e) ; PI-CF3与PI-T3晶体的ML光谱(c, f)[50-51] 衍生物和PI-Ar衍生物的结构(a, d); PI-CF3, PI-T3与PI-N晶体的ML照片(b, e) ; PI-CF3与PI-T3晶体的ML光谱(c, f)[50-51]

. Structures of PI derivatives and PI-Ar derivatives (a, d); ML photo of PI-CF3, PI-T3 and PI-N crystals (b, e); ML spectra of PI-CF3与PI-T3 crystals (c, f)[50-51]

图9. TPA-CHO-2H与TPA-CHO-2X以及tPE-2-Th与tPE-Ph的结构式(a, d); TPA-CHO-2F晶体以及tPE-2-Th晶体的ML照片(b, e); TPA-CHO-2H与TPA-CHO-2X晶体以及tPE-2-Th与tPE-Ph晶体中的分子堆积(c, f)[52-53]

Figure 9. Structures of TPA-CHO-2H, TPA-CHO-2X, tPE-2-Th, tPE-Ph (a, d); ML photos of TPA-CHO-2F and tPE-2-Th crystals (b, e); molecular packing in TPA-CHO-2H, TPA-CHO-2X, tPE-2-Th, tPE- Ph crystals (c, f)[52-53]

图10. ImF和ImBr以及OCN和BCPC的结构式(a, c); ImF和ImBr以及OCN和 BCPC晶体的ML光谱与ML照片(b, d)[54-55]

Figure 10. Structures of ImF, ImBr, OCN and BCPC (a, c); ML spectra and photos of ImF, ImBr, OCN and BCPC crystals (b, d)[54-55]

图11. BN、BO、BE、BB分子以及CNS系列分子的结构式(a, e); BN晶体与CNS-1和CNS-2晶体的ML/PL光谱(b, f)以及它们的ML照片(c, g); 晶体中的分子堆积(d, h)[57-58]

Figure 11. Structures of BN, BO, BE, BB and CNS series (a, e); ML/PL spectra (b, f) and photos of ML on BN, CNS-1 and CNS-2 crystal (c, g); molecular packing in crystals (d, h) [57-58]

图12. BMIP6和BMIP6t、CAC-N系列以及PIth-Cn系列的结构式(a, d, g); BMIP6晶体、偶数烷链CAC-N晶体以及PIth-C3和PIth-C4晶体的ML/PL光谱与ML照片(b, e, h); BMIP6和BMIP6t以及PIth-Cn系列晶体中的分子堆积、CAC-N系列晶体中的分子堆积示意图(c, f, i)[59⇓-61]和BMIP6t、CAC-N系列以及PIth-Cn系列的结构式(a, d, g); BMIP6晶体、偶数烷链CAC-N晶体以及PIth-C3和PIth-C4晶体的ML/PL光谱与ML照片(b, e, h); BMIP6和BMIP6t以及PIth-Cn系列晶体中的分子堆积、CAC-N系列晶体中的分子堆积示意图(c, f, i)[59⇓-61]

Figure 12. Structures of BMIP6, BMIP6t, CAC-N series and PIth-Cn series (a, d, g); ML/PL spectra and ML photos of BMIP6, CAC-N with even-carbon chain, PIth-C3, PIth-C4 crystals (b, e, h); molecular packing in BMIP6, BMIP6t, PIth-Cn crystals and schematic diagrams of molecular packing in CAC-N crystals with even-carbon chains (c, f, i)[59⇓-61]

图13. IMTPA系列、TPhBCz和TPh2BCz以及TPA-BA系列的结构式(a, d, g); IMTPA系列、TPhBCz和TPh2BCz以及TPA-BA系列晶体的分子堆积(b, e, i)以及ML活性晶体的ML/PL光谱(c, f, h) [62⇓-64]

Figure 13. Structures of IMTPA series, TPhBCz, TPh2BCz and TPA-BA series (a, d, g); molecular packing in IMTPA series, TPhBCz, TPh2BCz and TPA-BA series crystals (b, e, i); ML/PL spectra of ML-active crystals (c, f, h) [62⇓-64]

图14. TPA-F系列与TPE(PI)2系列的结构式(a, d);TPA-mF晶体与mm-TPE(PI)2晶体的ML照片与ML光谱(b, e); TPA-F系列与TPE(PI)2系列晶体中的分子堆积(c, f)[65-66]系列与TPE(PI)2系列的结构式(a, d);TPA-mF晶体与mm-TPE(PI)2晶体的ML照片与ML光谱(b, e); TPA-F系列与TPE(PI)2系列晶体中的分子堆积(c, f)[65-66]

Figure 14. Structures of TPA-F series and TPE(PI)2 series (a, d); ML photos and ML spectrum of TPA-mF and mm-TPE(PI)2 crystal (b, e); molecular packing in TPA-F and TPE(PI)2 series crystals (c, f)[65-66]

图15. 化合物的结构式(a, d, g), ML活性晶体的发光照片与ML/PL光谱(b, e, h), 晶体中的分子堆积(c, f, i)[67⇓-69]

Figure 15. Structures of compounds (a, d, g); ML/PL spectra and photos of ML-active crystals (b, e, h); molecular packing in crystals (c, f, i)[67⇓-69]

图16. PTCz和CCz的结构式(a); PTCz晶体的PL/ML光谱与照片(b); PTCz和CCz晶体中的分子堆积示意图(c); PTCz晶体中的二聚体堆积(d)[70]

Figure 16. Structures of PTCz and CCz (a); PL/ML spectra and photos of PTCz crystal (b); schematic diagrams of molecular packing in PTCz and CCz crystals (c); dimers in PTCz crystals (d)[70]

图17. 化合物的结构式(a, d, g, j, m, p), ML活性晶体的PL/ML光谱与ML照片(b, e, h, k, n, q), 晶体中的分子堆积(c, f, i, l, o)[71-72,74⇓-76,79-80]

Figure 17. Structures of compounds (a, d, g, j, m, p); PL/ML spectra and ML photos of ML-active crystals (b, e, h, k, n, q); molecular packing in crystals (c, f, i, l, o)[71-72,74⇓-76,79-80]

图18. DMACDPS与Me-DMACDPS的结构式(a); DMACDPS晶体的ML照片(b)与ML光谱(e); DMACDPS与Me-DMACDPS晶体中的分子堆积(c, d)[81]

Figure 18. Structures of DMACDPS and Me-DMACDPS (a); photo (b) and spectrum (e) of ML on DMACDPS crystal; molecular packing in DMACDPS and Me-DMACDPS crystals (c, d)[81]

图19. 中心对称与非中心对称空间群晶体上产生ML现象的机理示意图[82]

Figure 19. Schematic diagram of ML mechanism on crystals with non- and centrosymmetric space groups[82]

图20. Br-BPZ异构体的结构式(a)、力致构型转化示意图(b)、不同力持续时间下p-Br-BPZ晶体的ML光谱(c)[85]

Figure 20. Structures of Br-BPZ isomers (a), schematic diagram of force-induced configuration transformation (b), ML spectra of p-Br-BPZ crystal under different force duration (c)[85]

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调控有机小分子晶体力致发光行为的方法

Methods for Adjusting Mechanoluminescence Behaviors on Crystals of Purely Organic Small Molecules

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