Coumarin-tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

被引：4

作者：

Reddy, T. Sheshashena ^{[1
]}

Moon, Hyungkyu ^{[1
]}

Choi, Myung-Seok ^{[1
]}

机构：

[1] Konkuk Univ, Div Chem Engn, 120 Neungdong Ro, Seoul, South Korea

来源：

NEW JOURNAL OF CHEMISTRY | 2020年 / 44卷 / 13期

关键词：

MOLECULES; DESIGN; FLUORESCENCE; DYES;

D O I：

10.1039/d0nj00037j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Coumarin-tetraphenylethylene (CTPE) regioisomers with different linkage types (single-bond, vinyl, and acetylene) and substitution positions (coumarin C5, C6, C7) were synthesized and characterized using H-1 NMR, C-13 NMR, and high-resolution mass spectroscopy. The effects of substitution position and conjugation in CTPEs 1-9 on absorption, fluorescence, and aggregation-induced emission enhancement were explored. Electronic absorption and emission spectra indicate that CTPEs with C7 substitution are red-shifted compared to those substituted at C5 or C6. CTPEs 1-9 form aggregates in tetrahydrofuran/water (1 : 99, v/v) and exhibit aggregation-induced emission. Nanoaggregates were characterized using scanning electron microscopy and dynamic light scattering. The structure of CTPE 1 was confirmed by single crystal X-ray diffraction analysis.

引用

页码：4992 / 5000

页数：9

共 46 条

[1] Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters [J].

Ammar, Houcine ;

Abid, Souhir ;

Fery-Forgues, Suzanne .

DYES AND PIGMENTS, 2008, 78 (01) :1-7

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Design, Synthesis, and Biological and Crystallographic Evaluation of Novel Inhibitors of Plasmodium falciparum Enoyl-ACP-reductase (PfFabl) [J].

Belluti, Federica ;

Perozzo, Remo ;

Lauciello, Leonardo ;

Colizzi, Francesco ;

Kostrewa, Dirk ;

Bisi, Alessandra ;

Gobbi, Silvia ;

Rampa, Angela ;

Bolognesi, Maria Laura ;

Recanatini, Maurizio ;

Brun, Reto ;

Scapozza, Leonardo ;

Cavalli, Andrea .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (19) :7516-7526

[4] Turn-on fluorescence sensor based on the aggregation of pyrazolo[3,4-b]pyridine-based coumarin chromophores induced by Hg2+ [J].

Chen, Jianhong ;

Liu, Weimin ;

Wang, Ying ;

Zhang, Hongyan ;

Wu, Jiasheng ;

Xu, Haitao ;

Ju, Weigang ;

Wang, Pengfei .

TETRAHEDRON LETTERS, 2013, 54 (48) :6447-6449

[5] Computational Study of Ferrocene-Based Molecular Frameworks with 2,5-Diethynylpyridine as a Chemical Bridge [J].

Ding, Feizhi ;

Chen, Shaowei ;

Wang, Haobin .

MATERIALS, 2010, 3 (04) :2668-2683

[6] Triphenylamine derived coumarin chalcones and their red emitting OBO difluoride complexes: Synthesis, photophysical and NLO property study [J].

Erande, Yogesh ;

Kothavale, Shantaram ;

Sreenath, Mavila C. ;

Chitrambalam, Subramaniyan ;

Joe, Isaac H. ;

Sekar, Nagaiyan .

DYES AND PIGMENTS, 2018, 148 :474-491

[7] Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect [J].

Feng, Hai-Tao ;

Yuan, Ying-Xue ;

Xiong, Jia-Bin ;

Zheng, Yan-Song ;

Tang, Ben Zhong .

CHEMICAL SOCIETY REVIEWS, 2018, 47 (19) :7452-7476

[8] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .23. A POLARIZATION-TYPE BASIS SET FOR 2ND-ROW ELEMENTS [J].

FRANCL, MM ;

PIETRO, WJ ;

HEHRE, WJ ;

BINKLEY, JS ;

GORDON, MS ;

DEFREES, DJ ;

POPLE, JA .

JOURNAL OF CHEMICAL PHYSICS, 1982, 77 (07) :3654-3665

[9] Modified coumarins. 27. Ssynthesis and antioxidant activity of 3-substituted 5,7-dihydroxy-4-methylcoumarins [J].

Garazd, M. M. ;

Muzychka, O. V. ;

Vovk, A. I. ;

Nagorichna, I. V. ;

Ogorodniichuk, A. S. .

CHEMISTRY OF NATURAL COMPOUNDS, 2007, 43 (01) :19-23

[10] Novel Quercetin Aggregation-Induced Emission Luminogen (AIEgen) with Excited-State Intramolecular Proton Transfer for In Vivo Bioimaging [J].

He, Ting ;

Niu, Na ;

Chen, Zhijun ;

Li, Shujun ;

Liu, Shouxin ;

Li, Jian .

ADVANCED FUNCTIONAL MATERIALS, 2018, 28 (11)

← 1 2 3 4 5 →