Benzo[1,2-b:4,3-b']dithiophene-pyridine isomers: Synthesis, self-assembly, photophysical and acidochromic properties

被引:1
|
作者
Chang, Qing [1 ]
Ma, Tao [1 ]
Liu, Chao [1 ]
Hu, Jinliang [1 ]
Cheng, Xiaohong [1 ]
机构
[1] Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resources, Minist Educ, Kunming 650091, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
Self-assembly; Liquid crystal; Organogel; WLED; Acid-base vapors sensor; Information storage; CIRCULARLY-POLARIZED LUMINESCENCE; SUPRAMOLECULAR CHIRALITY; INVERSION; PHOSPHORS; SI;
D O I
10.1016/j.dyepig.2022.110490
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two benzo[1,2-b:4,3-b']dithiophene-pyridine-based bent shaped isomers (3BDTPy12 and 4BDTPy12) have been synthesized via Suzuki coupling reactions as key steps. They differ themselves in the position of N-atom on the pyridine unit which has generated significant effect on their self-assembly behavior and photophysical properties. 4BDTPy12 with N in the para position in the pyridine ring can self-assemble into a columnar liquid crystalline phase while its isomer 3BDTPy12 with N in the meta position in the pyridine ring is only a crystal. Both compounds can form gels in different organic solvents but with different morphologies. The influence of the solvent polarities and doping agents including chiral L-phenylalanine (L-Phe), trifluoroacetic acid as well as L tartaric acid on their gel morphologies were also studied. The gel of 4BDTPy12 doped with L-tartaric acid could produce enhanced yellow emission which can be used to generate WLED, and such compounds can be used as chemosensors towards volatile acid-base vapors with good reversibility.
引用
收藏
页数:8
相关论文
共 50 条
  • [21] Effect of donor and acceptor on optoelectronic properties of benzo[1,2-b:4,5-b′]dithiophene
    Kashifa Fazl-Ur-Rahman
    Divya Maldepalli Govindachar
    Ganga Periyasamy
    Theoretical Chemistry Accounts, 2021, 140
  • [22] Electrochemical Route to Solution-Processable Polymers of Thiophene/Selenophene Capped Didodecyloxybenzo[1,2-b:4,3-b']dithiophene and Their Optoelectronic Properties
    Bedi, Anjan
    Zade, Sanjio S.
    MACROMOLECULES, 2013, 46 (22) : 8864 - 8872
  • [23] Synthesis and photovoltaic properties of conjugated copolymers with benzo[1,2-b:4,5-b′]dithiophene and thiadiazolo[3,4-c] pyridine moieties
    Kang, Huaiyin
    Zhao, Bin
    Cao, Zhencai
    Zhong, Jun
    Li, Haohao
    Pei, Yong
    Shen, Ping
    Tan, Songting
    EUROPEAN POLYMER JOURNAL, 2013, 49 (09) : 2738 - 2747
  • [24] CRYSTAL AND MOLECULAR-STRUCTURE OF HETEROHELICENE 1-TERT-BUTYLBENZO[D]NAPHTHO[1,2-D']BENZO[1,2-B - 4,3-B']DITHIOPHENE AT 110K
    WIJMENGA, SS
    NUMAN, H
    VOS, A
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1978, 34 (MAR): : 846 - 849
  • [25] Synthesis and properties of [7] helicene and [7] helicene-like compounds with a cyclopenta[1,2-b: 4,3-b'] dithiophene or dithieno[2,3-b: 3',2'-d] heterole skeleton
    Uematsu, K.
    Noguchi, K.
    Nakano, K.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2018, 20 (05) : 3286 - 3295
  • [26] Concentration-Dependent Pyrene-Driven Self-Assembly in Benzo[1,2-b:4,5-b′]dithiophene (BDT)-Thienothiophene (TT)-Pyrene Copolymers
    Bathula, Chinna
    Kim, Minjun
    Song, Chang Eun
    Shin, Won Suk
    Hwang, Do-Hoon
    Lee, Jong-Cheol
    Kang, In-Nam
    Lee, Sang Kyu
    Park, Taiho
    MACROMOLECULES, 2015, 48 (11) : 3509 - 3515
  • [27] Dopant-free hole-transporting material with passivation effect based on Benzo[1,2-b:4,3-b′]dithiophene for inverted perovskite solar cells
    Zhang, Deling
    Wei, Xiaochun
    Yu, Bo
    Wu, Hanlun
    Tang, Hao
    Wang, Lingyun
    Yu, Huangzhong
    Cao, Derong
    JOURNAL OF POWER SOURCES, 2025, 631
  • [28] Synthesis, properties, and structures of benzo[1,2-b:4,5-b′]bis[b]benzothiophene and benzo[1,2-b:4,5-b′]bis[b]benzoselenophene
    Ebata, Hideaki
    Miyazaki, Eigo
    Yamamoto, Tatsuya
    Takimiya, Kazuo
    ORGANIC LETTERS, 2007, 9 (22) : 4499 - 4502
  • [29] Benzo[1,2-b:4,5-b′]dithiophene and benzo[1,2-b:4,5-b′]difuran based organic dipolar compounds for sensitized solar cells
    Lin, Yan-Zuo
    Yeh, Chia-Wei
    Chou, Po-Ting
    Watanabe, Motonori
    Chang, Yu-Hsuan
    Chang, Yuan Jay
    Chow, Tahsin J.
    DYES AND PIGMENTS, 2014, 109 : 81 - 89
  • [30] Benzo[1,2-b:4,5-b ']dithiophene-4,8-dione
    Ramirez, Amanda L.
    Chan, Benny C.
    De Lill, Daniel T.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1428 - +