4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene

被引:2
作者
Sagitova, Elena F. [1 ]
Petrova, Olga V. [1 ]
Tomilin, Denis N. [1 ]
Ushakov, Igor A. [1 ]
Sobenina, Lyubov N. [1 ]
Trofimov, Boris A. [1 ]
机构
[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia
关键词
fluorophore BODIPY; 2; 2-trifluoro-1-(1H-pyrrol-2-yl)ethan-1-ol; 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole; condensation; BODIPY DYES; DESIGN;
D O I
10.3390/M1595
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound, 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(2-naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), was synthesized for the first time in a 62% yield by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) followed by the oxidation of dipyrromethane 4 and the complexation of dipyrromethene thus formed with BF3. The product fluoresces in a long wave region (651-662 nm) with a high quantum yield (0.49-0.61).
引用
收藏
页数:5
相关论文
共 16 条
[1]   Aggregation-induced emission enhancement of a meso-trifluoromethyl BODIPY via J-aggregation [J].
Choi, Sohee ;
Bouffard, Jean ;
Kim, Youngmi .
CHEMICAL SCIENCE, 2014, 5 (02) :751-755
[2]   Recent Advances in BODIPY Compounds: Synthetic Methods, Optical and Nonlinear Optical Properties, and Their Medical Applications [J].
Gurubasavaraj, Prabhuodeyara M. ;
Sajjan, Vinodkumar P. ;
Munoz-Flores, Blanca M. ;
Perez, Victor M. Jimenez ;
Hosmane, Narayan S. .
MOLECULES, 2022, 27 (06)
[3]   Synthesis of meso-CF3-Substituted BODIPY Compounds with Redshifted Absorption [J].
Jiang, Xin-Dong ;
Fang, Tao ;
Liu, Xin ;
Xi, Dongmei .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (34) :5074-5079
[4]   Recent advances in the application of BODIPY in bioimaging and chemosensing [J].
Kaur, Paramjit ;
Singh, Kamaljit .
JOURNAL OF MATERIALS CHEMISTRY C, 2019, 7 (37) :11361-11405
[5]  
Korostova S.E., 1989, CHEM HETEROCYC COMPO, V25, P39, DOI [10.1007/BF00472615, DOI 10.1007/BF00472615]
[6]   Functionalization of the 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) core [J].
Li, Lingling ;
Nguyen, Binh ;
Burgess, Kevin .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (10) :3112-3116
[7]   BODIPY dyes and their derivatives: Syntheses and spectroscopic properties [J].
Loudet, Aurore ;
Burgess, Kevin .
CHEMICAL REVIEWS, 2007, 107 (11) :4891-4932
[8]   Editorial: BODIPYs and Their Derivatives: The Past, Present and Future [J].
Lu, Hua ;
Shen, Zhen .
FRONTIERS IN CHEMISTRY, 2020, 8
[9]  
Pandhurnekar CP, 2023, J HETEROCYCLIC CHEM, V60, P537, DOI [10.4103/jimph.jimph_5_21, 10.1002/jhet.4586]
[10]   Recent advances of BODIPY based derivatives for optoelectronic applications [J].
Poddar, Madhurima ;
Misra, Rajneesh .
COORDINATION CHEMISTRY REVIEWS, 2020, 421