The Photophysics of Pyridine-Derivatized ortho-, meta-, and para-Dibutylamino Cruciforms

被引:11
|
作者
Hinderer, Florian [1 ]
Bunz, Uwe H. F. [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-06120 Heidelberg, Germany
关键词
cruciforms; distyrylbenzene; fluorophores; solvatochromism; sensors; INTRAMOLECULAR CHARGE-TRANSFER; SOLVATION ENERGY RELATIONSHIPS; PI-SYSTEMS; BENZOBISOXAZOLE CRUCIFORMS; CONJUGATION; STATE; FLUOROPHORES; BEHAVIOR; FLUORESCENCE; OLIGOMERS;
D O I
10.1002/chem.201300211
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photophysical properties of a series of para-substituted donor-acceptor cruciform fluorophores (p1-4) were investigated and compared with their meta and ortho isomers (m1-4 and o1-4). The structural variations were found to have a significant effect on the solvatochromism, fluorescence quantum yields (phi fl), fluorescence lifetimes (fl), and response upon addition of trifluoroacetic acid. The observed spectral shifts in absorption and emission caused by protonation of the cruciforms make them promising candidates as chemosensors. Additional computational studies provided more insight into the electronic structure of the systems.
引用
收藏
页码:8490 / 8496
页数:7
相关论文
共 50 条
  • [21] Thermochemistry of di-substituted benzenes: Ortho-, meta-, and para-hydroxyacetophenones
    Andreeva, Irina, V
    Varfolomeev, Mikhail A.
    Verevkin, Sergey P.
    JOURNAL OF CHEMICAL THERMODYNAMICS, 2020, 140
  • [22] Synthesis of N,N'-dimethylenesulfonates of ortho-, meta- and para-diamino-arsenobenzene
    Kashima, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1925, 47 : 2207 - 2211
  • [23] Excess enthalpies of binary mixtures of ortho-, meta-, and para-structural isomers
    Liu, Hongli
    Yamashita, Tomoko
    Kamiyama, Tadashi
    Fujisawa, Masao
    Kimura, Takayoshi
    JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2010, 99 (01) : 95 - 103
  • [24] Synthesis and antimycobacterial activity of new amidoderivatives of ortho-, meta- and para-toluidine.
    Biava, M
    Fioravanti, R
    Porretta, GC
    Sleiter, G
    Ettorre, A
    Deidda, D
    Lampis, G
    Pompei, R
    MEDICINAL CHEMISTRY RESEARCH, 1998, 8 (09) : 523 - 541
  • [25] Photoisomerization of Trans Ortho-, Meta-, Para-Nitro Diarylbutadienes: A Case of Regioselectivity
    Agnihotri, Harsha
    Paramasivam, Mahalingavelar
    Palakollu, Veerabhadraiah
    Kanvah, Sriram
    PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2015, 91 (06) : 1324 - 1331
  • [26] ortho-, meta-, and para-Dihydroindenofluorene Derivatives as Host Materials for Phosphorescent OLEDs
    Romain, Maxime
    Thiery, Sebastien
    Shirinskaya, Anna
    Declairieux, Celine
    Tondelier, Denis
    Geffroy, Bernard
    Jeannin, Olivier
    Rault-Berthelot, Joelle
    Metivier, Remi
    Poriel, Cyril
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1176 - 1180
  • [27] ELECTRIC DIPOLE MOMENTS OF ORTHO- META- PARA- AND PENTA-FLUOROSTYRENE MOLECULES
    BOCK, E
    IWACHA, D
    CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (18): : 2961 - &
  • [28] UV-absorption cross sections of benzaldehyde, ortho-, meta-, and para-tolualdehyde
    Thiault, G
    Mellouki, A
    Le Bras, G
    Chakir, A
    Sokolowski-Gomez, N
    Daumont, D
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2004, 162 (2-3) : 273 - 281
  • [29] Infrared and ultraviolet spectroscopy of jet-cooled ortho-, meta-, and para-diethynylbenzene
    Stearns, JA
    Zwier, TS
    JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (49): : 10717 - 10724
  • [30] Electronic structure and conformations of ortho-, meta-, and para-aminobenzensulfonic acid and its dimers
    Mora, M. A.
    Mora-Ramirez, M. A.
    Soto-Estrada, A. M.
    Bertin, V.
    POLYMER, 2007, 48 (18) : 5431 - 5439