Effect of conjugation on the optoelectronic properties of pyrazine-based push-pull chromophores: Aggregation-induced emission, solvatochromism, and acidochromism

被引:24
作者
Park, Hyung-Ha [1 ]
Meti, Puttavva [1 ]
Gong, Young-Dae [1 ]
机构
[1] Dongguk Univ, Coll Sci, Innovat Drug Lib Res Ctr, Dept Chem, 26,3-Ga Pil Dong, Seoul 04620, South Korea
基金
新加坡国家研究基金会;
关键词
Pyrazine; Aggregation-induced emission; Charge transfer; Solvatochromism; FLUORESCENT ORGANIC NANOPARTICLES; OPTICAL-PROPERTIES; AIE; TETRAPHENYLETHENE; LUMINOGENS; SERIES; DYES;
D O I
10.1016/j.dyepig.2021.109320
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of pyrazine-based bipodal D-?-A-?-D and D-?-A-?-A molecules with multi-stimuli response have been synthesized via Suzuki and Sonogashira cross-coupling reactions. We present a joint theoretical and experimental study to elucidate structure-property relationship of these push-pull chromophores. The modification of the endcapped donor-acceptor units and the extension of ?-conjugation are key factors in tuning their optical, thermal and electrochemical properties. Depending on the different electron-donating substituents, the chromophores emit blue to orange fluorescence. The solvent dependent emission was observed and their Dimroth-Reichardt plots show a linear correlation. The aggregation-induced study shows enhanced emission in aggregates. Our work has elucidated that these small structural isomers can be utilized to develop a promising multi-stimuli responsive fluorescent materials.
引用
收藏
页数:12
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共 57 条
[1]   Tuning the Photophysical Properties of Push-Pull Azaheterocyclic Chromophores by Protonation: A Brief Overview of a French-Spanish-Czech Project [J].
Achelle, Sylvain ;
Rodriguez-Lopez, Julian ;
Bures, Filip ;
Robin-le Guen, Francoise .
CHEMICAL RECORD, 2020, 20 (05) :440-451
[2]   Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties [J].
Achelle, Sylvain ;
Rodriguez-Lopez, Julian ;
Larbani, Massinissa ;
Plaza-Pedroche, Rodrigo ;
Robin-le Guen, Francoise .
MOLECULES, 2019, 24 (09)
[3]   Emission properties of diazines chromophores: Structure-properties relationship [J].
Achelle, Sylvain ;
Robin-le Guen, Francoise .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2017, 348 :281-286
[4]   Luminescence Behavior of Protonated Methoxy-Substituted Diazine Derivatives: Toward White Light Emission [J].
Achelle, Sylvain ;
Rodriguez-Lopez, Julian ;
Katan, Claudine ;
Robin-le Guen, Francoise .
JOURNAL OF PHYSICAL CHEMISTRY C, 2016, 120 (47) :26986-26995
[5]   Synthesis and Photophysical Investigation of a Series of Push-Pull Arylvinyldiazine Chromophores [J].
Achelle, Sylvain ;
Barsella, Alberto ;
Baudequin, Christine ;
Caro, Bertrand ;
Guen, Francoise Robin-le .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :4087-4096
[6]   A fluorescence turn-on mechanism to detect high explosives RDX and PETN [J].
Andrew, Trisha L. ;
Swager, Timothy M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7254-+
[7]   Fluorescent 7-Substituted Coumarin Dyes: Solvatochromism and NLO Studies [J].
Bhagwat, Archana A. ;
Sekar, Nagaiyan .
JOURNAL OF FLUORESCENCE, 2019, 29 (01) :121-135
[8]   Structure-Property Relationships and Nonlinear Optical Effects in Donor-Substituted Dicyanopyrazine-Derived Push-Pull Chromophores with Enlarged and Varied π-Linkers [J].
Bures, Filip ;
Cermakova, Hana ;
Kulhanek, Jiri ;
Ludwig, Miroslav ;
Kuznik, Wojciech ;
Kityk, Iwan V. ;
Mikysek, Tomas ;
Ruzicka, Ales .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (03) :529-538
[9]   Unveiling the Different Emission Behavior of Polytriazoles Constructed from Pyrazine-Based AIE Monomers by Click Polymerization [J].
Chen, Ming ;
Li, Lingzhi ;
Wu, Haiqiang ;
Pan, Lingxiang ;
Li, Shiwu ;
He, Bairong ;
Zhang, Haoke ;
Sun, Jing Zhi ;
Qin, Anjun ;
Tang, Ben Zhong .
ACS APPLIED MATERIALS & INTERFACES, 2018, 10 (15) :12181-12188
[10]   Tetraphenylpyrazine-based AIEgens: facile preparation and tunable light emission [J].
Chen, Ming ;
Li, Lingzhi ;
Nie, Han ;
Tong, Jiaqi ;
Yan, Lulin ;
Xu, Bin ;
Sun, Jing Zhi ;
Tian, Wenjing ;
Zhao, Zujin ;
Qin, Anjun ;
Tang, Ben Zhong .
CHEMICAL SCIENCE, 2015, 6 (03) :1932-1937