Stimuli-responsive 2,6-diarylethene-4H-pyran-4-one derivatives: Aggregation induced emission enhancement, mechanochromism and solvatochromism

被引:23
|
作者
Cao, YuQi [1 ,2 ]
Chen, Ligong [1 ,2 ,3 ]
Xi, Ye [1 ,2 ]
Li, Yang [1 ,2 ,3 ]
Yan, Xilong [1 ,2 ,3 ]
机构
[1] Tianjin Univ, Sch Chem Engn & Technol, Tianjin, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin, Peoples R China
[3] Tianjin Engn Res Ctr Funct Fine Chem, Tianjin, Peoples R China
基金
中国国家自然科学基金;
关键词
Organic; Functional; Aggregation induced emission enhancement; Mechanochromism; Solvatochromism; FLUORESCENCE; MECHANOFLUOROCHROMISM; LUMINESCENCE; COMPLEX;
D O I
10.1016/j.matlet.2017.10.041
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A series of 2,6-diarylethene-4H-pyran-4-one organic functional materials (pp-s) were designed and successfully synthesized, characterized by PL spectra. It was found that all of them displayed the aggregation induced emission enhancement (AIEE) phenomenon, and three of them presented different emission spectra in different solvents i.e. solvatochromism, which was confirmed by density functional theory (DFT) calculation on the ICT process. Remarkably, an inverted U-shaped mechanochromic behavior (MFC) and red-shifted phenomenon of their emission spectra (bathochromism) was observed along with the increasing of conjugation degree. In which, the compound containing triphenylamine units (pp-3) showcasing the best MFC nature. PXRD profiles indicated the transformation between two different crystalline states upon grinding. Thus, we offer a way to manipulate the chromism performance via conjugation-regulating strategy. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:225 / 230
页数:6
相关论文
共 50 条
  • [21] 3,5-Dimethyl-2,6-diphenyl-3,4,5,6-tetrahydro-2H-pyran-4-one
    Asghar, Muhammad Nadeem
    Arshad, Muhammad Nadeem
    Zia-ur-Rehman, Muhammad
    Khan, Islam Ullah
    Shafiq, Muhammad
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O463 - U1285
  • [24] Aggregation-induced emission and mechanofluorochromic materials based on the structural modification of 4,5,6-triaryl-4H-pyran skeleton
    Han, Xiangdong
    Liu, Xiaoqing
    Guo, Yan
    Lei, Yunxiang
    Gao, Wenxia
    Zhou, Yunbing
    Liu, Miaochang
    Huang, Xiaobo
    Wu, Huayue
    DYES AND PIGMENTS, 2022, 207
  • [25] Imidazole decorated dicyanomethylene-4H-pyran skeletons with aggregation induced emission effect and applications for sensing viscosity
    Li, Qi
    Huang, Kun
    Qiu, Qi
    Zhang, Xiangyu
    Qin, Dabin
    Zeng, Xianshun
    DYES AND PIGMENTS, 2021, 193
  • [26] Organic light emitting diodes with red emission using (2,6-dimethyl-4H-pyran-4′-ylidene)malononitrile moiety
    Lim, ST
    Chun, MH
    Lee, KW
    Shin, DM
    OPTICAL MATERIALS, 2003, 21 (1-3) : 217 - 220
  • [27] SYNTHESIS OF SOME BIOLOGICALLY-ACTIVE DERIVATIVES OF 2-HYDROXYMETHYL-5-HYDROXY-4H-PYRAN-4-ONE
    VEVERKA, M
    KRALOVICOVA, E
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (03) : 833 - 840
  • [28] Aggregation-induced emission enhancement (AIEE)-active Pt(II) metallomesogens as dyes sensitive to Hg2+ and dopant agents to develop stimuli-responsive luminescent polymer materials
    Cuerva, Cristian
    Campo, Jose A.
    Cano, Mercedes
    Cano-Garcia, Manuel
    Oton, Jose M.
    Lodeiro, Carlos
    DYES AND PIGMENTS, 2020, 175
  • [29] BIS(2,6-DIMETHYL-4H-PYRAN-4-ONE)DINITRATOZINC, [ZN(NO3)2(C7H8O2)2]
    BROWN, CJ
    LEWIS, JFP
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (MAR) : 368 - 370
  • [30] Chemistry of pyrones, part 5:: New crown ether and podand derivatives of 3,5-bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one
    Shahrisa, A
    Banaei, A
    MOLECULES, 2001, 6 (09) : 721 - 727