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

Authors

  • Е. Н. Шепеленко Southern Scientific Center, Russian Academy of Sciences
  • Н. И. Макарова Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University
  • О. Г. Карамов Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University
  • А. Д. Дубоносов Southern Scientific Center, Russian Academy of Sciences
  • В. А. Подшибякин Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University
  • А. В. Метелица Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University
  • В. А. Брень Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University
  • В. И. Минкин Southern Scientific Center, Russian Academy of Sciences; Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

DOI:

https://doi.org/10.1007/1725

Keywords:

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

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

Author Biographies

Е. Н. Шепеленко, Southern Scientific Center, Russian Academy of Sciences

Евгений Николаевич Шепеленко

Старший научный сотрудник отдела Физической Органической Химии

Н. И. Макарова, Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Надежда Ивановна Макарова

Старший научный сотрудник

О. Г. Карамов, Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Оганес Георгиевич Карамов

Научный сотрудник

А. Д. Дубоносов, Southern Scientific Center, Russian Academy of Sciences

Александр Дмитриевич Дубоносов

Ведущий научный сотрудник

В. А. Подшибякин, Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Виталий Алексеевич Подшибякин

Студент

А. В. Метелица, Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Анатолий Викторович Метелица

Директор института

В. А. Брень, Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Владимир Александрович Брень

Заведующий отделом

В. И. Минкин, Southern Scientific Center, Russian Academy of Sciences; Scientific-Research Institute of Physical and Organic Chemistry, Southern Federal University

Владимир Исаакович Минкин

Научный консультант ЮФУ

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Published

2014-08-08

Issue

No. 7 (2014)

Section

Original Papers