Dual-State Emission of 2-(Butylamino)Cinchomeronic Dinitrile Derivatives

被引:2
作者
Lipin, Konstantin, V [1 ]
Ievlev, Mikhail Yu [1 ]
Ershova, Anastasiya, I [1 ]
Ershov, Oleg, V [1 ]
机构
[1] Chuvash State Univ, Dept Organ & Pharmaceut Chem, Moskovsky Pr 15, Cheboksary 428015, Russia
来源
MOLECULES | 2022年 / 27卷 / 21期
关键词
cyano compounds; aminopyridines; dual-state emission; fluorescent dyes; cinchomeronic dinitriles; AGGREGATION-INDUCED EMISSION; RATIOMETRIC FLUORESCENCE PROBES; DESIGN; ENHANCEMENT; MOLECULE;
D O I
10.3390/molecules27217144
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
New representatives of 2-(butylamino)cinchomeronic dinitrile derivatives were synthesized as promising fluorophores showing dual-state emission. To characterize the influence of the length (from methyl to butyl) and the structure (both linear and branched) of the alkyl substituent at the amino nitrogen atom, the spectral fluorescence properties of all synthesized compounds were carefully studied both in solution and in solid state. The highest photoluminescence quantum yield values of 63% were noted for solutions of 2-(butylamino)-6-phenylpyridine-3,4-dicarbonitrile in DCM and 2-(butylamino)-5-methyl-6-phenylpyridine-3,4-dicarbonitrile in toluene.
引用
收藏
页数:19
相关论文
共 47 条
[21]   Dual emission in purely organic materials for optoelectronic applications [J].
Kukhta, Nadzeya A. ;
Bryce, Martin R. .
MATERIALS HORIZONS, 2021, 8 (01) :33-55
[22]   Exploring an Emissive Charge Transfer Process in Zero-Twist Donor-Acceptor Molecular Design as a Dual-State Emitter [J].
Kumar, Sunil ;
Singh, Punita ;
Kumar, Pushpendra ;
Srivastava, Ritu ;
Pal, Suman Kalyan ;
Ghosh, Subrata .
JOURNAL OF PHYSICAL CHEMISTRY C, 2016, 120 (23) :12723-12733
[23]   Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules [J].
Lee, Min Hee ;
Kim, Jong Seung ;
Sessler, Jonathan L. .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (13) :4185-4191
[24]   An Integration Strategy to Develop Dual-State Luminophores with Tunable Spectra, Large Stokes Shift, and Activatable Fluorescence for High-Contrast Imaging [J].
Liu, Yongchao ;
Teng, Lili ;
Xu, Chengyan ;
Ren, Tian-Bing ;
Xu, Shuai ;
Lou, Xiaofeng ;
Yuan, Lin ;
Zhang, Xiao-Bing .
CCS CHEMISTRY, 2022, 4 (06) :2153-2164
[25]   Aggregation-Induced Emission: Together We Shine, United We Soar! [J].
Mei, Ju ;
Leung, Nelson L. C. ;
Kwok, Ryan T. K. ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL REVIEWS, 2015, 115 (21) :11718-11940
[26]   Dual-state emission difluoroboron derivatives for selective detection of picric acid and reversible acid/base fluorescence switching [J].
Ni, Yingyong ;
Zhang, Shuaishuai ;
He, Xuan ;
Huang, Jianyan ;
Kong, Lin ;
Yang, Jianjun ;
Yang, Jiaxiang .
ANALYTICAL METHODS, 2021, 13 (25) :2830-2835
[27]   Substituent effect on emission of flavonolate-boron difluoride complexes: The role of π-system for dual-state (solution and solid) emission [J].
Ohno, Keiji ;
Narita, Fuka ;
Yokobori, Hidehisa ;
Iiduka, Nanami ;
Sugaya, Tomoaki ;
Nagasawa, Akira ;
Fujihara, Takashi .
DYES AND PIGMENTS, 2021, 187
[28]   Aggregation/Viscosity-Induced Emission and Third-Order Nonlinear Optical Signal Inversion in a TICT System [J].
Peng, Qiuchen ;
Yang, Linpo ;
Li, Yuanyuan ;
Zhang, Yu ;
Li, Tianhao ;
Qin, Yujing ;
Song, Yinglin ;
Hou, Hongwei ;
Li, Kai .
JOURNAL OF PHYSICAL CHEMISTRY C, 2020, 124 (41) :22684-22691
[29]   Towards more accurate bioimaging of drug nanocarriers: turning aggregation-caused quenching into a useful tool [J].
Qi, Jianping ;
Hu, Xiongwei ;
Dong, Xiaochun ;
Lu, Yi ;
Lu, Huiping ;
Zhao, Weili ;
Wu, Wei .
ADVANCED DRUG DELIVERY REVIEWS, 2019, 143 :206-225
[30]   Highly efficient, dual state emission from an organic semiconductor [J].
Reineke, Sebastian ;
Seidler, Nico ;
Yost, Shane R. ;
Prins, Ferry ;
Tisdale, William A. ;
Baldo, Marc A. .
APPLIED PHYSICS LETTERS, 2013, 103 (09)