π-π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

被引：41

作者：

Padalkar, Vikas S. ^{[1
]}

Sakamaki, Daisuke ^{[1
]}

Kuwada, Kenji ^{[1
]}

Horio, Akifumi ^{[1
]}

Okamoto, Haruka ^{[1
]}

Tohnai, Norimitsu ^{[2
]}

Akutagawa, Tomoyuki ^{[3
]}

Sakai, Ken-ichi ^{[4
]}

Seki, Shu ^{[1
]}

机构：

[1] Kyoto Univ, Dept Mol Engn, Katsura Campus, Kyoto 6158510, Japan

[2] Osaka Univ, Dept Mat & Life Sci, Suita Campus, Suita, Osaka 5650871, Japan

[3] Tohuku Univ, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808577, Japan

[4] Chitose Inst Sci & Technol, Dept Bio & Mat Photon, Chitose 0668655, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 07期

基金：

日本学术振兴会;

关键词：

aggregation-induced emission; excited-state intramolecular proton transfer; fluorescence; molecular packing; photophysics; INTRAMOLECULAR PROTON-TRANSFER; AGGREGATION-INDUCED EMISSION; SENSITIZED SOLAR-CELLS; EFFICIENT EMISSION; ENHANCED EMISSION; CRYSTAL PACKING; FLUORESCENCE; TRIPHENYLAMINE; DERIVATIVES; DONOR;

D O I：

10.1002/ajoc.201600159

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (phi(sol)approximate to 95%; phi(solid)approximate to 88%), moderate Stokes shifts (approximate to 8000cm(-1)), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of - interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88%.

引用

页码：938 / 945

页数：8

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