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

页数：19

共 47 条

[1] Dual Emission: Classes, Mechanisms, and Conditions [J].

Behera, Santosh Kumar ;

Park, Soo Young ;

Gierschner, Johannes .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (42) :22624-22638

[2] Dual-State Emission (DSE) in Organic Fluorophores: Design and Applications [J].

Belmonte-Vazquez, Jose L. ;

Amador-Sanchez, Yoarhy A. ;

Rodriguez-Cortes, Lizbeth A. ;

Rodriguez-Molina, Braulio .

CHEMISTRY OF MATERIALS, 2021, 33 (18) :7160-7184

[3] Yellow-red emitting, methoxy substituted triphenylamine-based styryl derivatives: Synthesis, photophysical properties, viscosity sensitivity, aggregation induced emission, NLO properties, and DFT study [J].

Bhalekar, Sulochana ;

Kothavale, Shantaram ;

Sekar, Nagaiyan .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2019, 384

[4] Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report) [J].

Brouwer, Albert M. .

PURE AND APPLIED CHEMISTRY, 2011, 83 (12) :2213-2228

[5] Through bond energy transfer (TBET)-based fluorescent chemosensors [J].

Cao, Duxia ;

Zhu, Linlin ;

Liu, Zhiqiang ;

Lin, Weiying .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2020, 44

[6] Thermally Activated Delayed Fluorescence (TADF) Path toward Efficient Electroluminescence in Purely Organic Materials: Molecular Level Insight [J].

Chen, Xian-Kai ;

Kim, Dongwook ;

Bredas, Jean-Luc .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (09) :2215-2224

[7] Novel chromophores of cyanopyridine series with strong solvatochromism and near-infrared solid-state fluorescence [J].

Chunikhin, Sergey S. ;

Ershov, Oleg, V ;

Ievlev, Mikhail Yu ;

Belikov, Mikhail Yu ;

Tafeenko, Viktor A. .

DYES AND PIGMENTS, 2018, 156 :357-368

[8] Fluorescent Organic Nanoparticles Constructed by a Facile "Self-Isolation Enhanced Emission" Strategy for Cell Imaging [J].

Dang, Dongfeng ;

Wang, Xiaochi ;

Wang, Daquan ;

Yang, Zhiwei ;

Hao, Dongxiao ;

Xu, Yanzi ;

Zhang, Shengli ;

Meng, Lingjie .

ACS APPLIED NANO MATERIALS, 2018, 1 (05) :2324-2331

[9] Synthesis, solution and solid-state fluorescence of 2-diethylaminocinchomeronic dinitrile derivatives [J].

Ershov, O. V. ;

Ievlev, M. Yu. ;

Belikov, M. Yu. ;

Naidenova, A. I. ;

Maksimova, V. N. ;

Tafeenko, V. A. .

RSC ADVANCES, 2017, 7 (55) :34886-34891

[10] Synthesis and solid-state fluorescence of aryl substituted 2-halogenocinchomeronic dinitriles [J].

Ershov, O. V. ;

Ievlev, M. Yu. ;

Belikov, M. Yu. ;

Lipin, K. V. ;

Naydenova, A. I. ;

Tafeenko, V. A. .

RSC ADVANCES, 2016, 6 (85) :82227-82232

← 1 2 3 4 5 →