Open Access Open Access  Restricted Access Subscription Access

SYNTHESIS AND PHOTOCHROMIC PROPERTIES OF ASYMMETRIC DIHETARYLETHENES BASED ON 5-METHOXY-1,2-DIMETHYLINDOLE AND 5-(4-BROMOPHENYL)-2-METHYLTHIOPHENE

Е. Н. Шепеленко, Н. И. Макарова, О. Г. Карамов, А. Д. Дубоносов, В. А. Подшибякин, А. В. Метелица, В. А. Брень, В. И. Минкин
Cover Image

Abstract


We report the synthesis of new asymmetric dihetarylethenes – 4-[5-(4-bromophenyl)-2‑methylthiophen-3-yl]-3‑(5-methoxy-1,2-dimethyl-1H-indol-3-yl)furan-2,5-dione and 1‑alkyl(phenyl)-3-(5-methoxy-1,2-dimethyl-1H‑indol-3-yl)-4-[5-(4-bromophenyl)-2-methylthiophen-3-yl]-1H-pyrrole-2,5-diones, which exhibit photo-chromic and fluorescent properties in solution. Thermally stable photoinduced cyclic isomers were observed for dihetarylethenes derived from 5-methoxy-1,2-dimethylindole and 5‑(4‑bromophenyl)-2-methylthiophene, unlike for their structural analogs based on 5‑methoxy-1,2-dimethylindole and unsubstituted thiophene. Changing the thiophene fragment of dihetarylethenes to a 5-(4-bromophenyl)-2-methylthiophene fragment gave rise to photochromic properties in furan-2,5‑dione derivatives.

How to Cite
Shepelenko, E. N.; Makarova, N. I.; Karamov, O. G.; Dubonosov, A. D.; Podshibakin, V. A.; Metelitsa, A. V.; Bren', V. A.; Minkin, V. I. Chem. Heterocycl. Compd. 2014, 50, 932. [Khim. Geterotsikl. Soedin. 2014, 1013.]

For this article in the English edition see DOI 10.1007/s10593-014-1547-7


Keywords


dihetarylethene; furan-2,5-dione; indole; pyrrole-2,5-dione; thiophene; fluorescence; photochromism

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv