Synthesis of New, Highly Luminescent bis(2,2’-bithiophen-5-yl) Substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthesis of New, Highly Luminescent bis(2,2’-bithiophen-5-yl) Substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2014, Volume: 10, Pages: 1596-1602 Pages count : 7 DOI: 10.3762/bjoc.10.165

Tags

bithiophene; donor–acceptor; luminescence; 1,3,4-oxadiazole; 1,3,4-thiadiazole; 4H-1,2,4-triazole

Authors

Kostyuchenko Anastasia S. ^1,2 , Yurpalov Vyacheslav L. ¹ , Kurowska Aleksandra ³ , Domagala Wojciech ³ , Pron Adam ⁴ , Fisyuk Alexander S ^1,2

Affiliations

1	Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russia
2	Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, Omsk 644050, Russia
3	Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland
4	Faculty of Chemistry Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland

A new synthetic approach towards the preparation of functionalised, soluble, donor–acceptor (DA) alkylbithiophene derivatives of oxadiazole, thiadiazole and triazole is reported. Taking advantage of the Fiesselmann reaction, reactive bithiophene synthons having alkyl or alkoxy substituents at designated positions are prepared. Following a synthetic strategy, featuring the bottom-up approach, sequential structural elements are built, starting from a simple thiophene compound, until the target molecule is obtained, all in good yield. Supplementing the well established methods of oxadiazole and thiadiazole synthesis, efficient ring closure reaction affording a 4H-1,2,4-triazole unit is presented. All target ambipolar compounds display strong photoluminescence with measured quantum yields up to 0.59. Modification of the demonstrated synthetic routes may be exploited for the preparation of longer, specifically functionalised oligothiophenes, coupled to other heteroaromatic cores.

Kostyuchenko A.S. , Yurpalov V.L. , Kurowska A. , Domagala W. , Pron A. , Fisyuk A.S.
Synthesis of New, Highly Luminescent bis(2,2’-bithiophen-5-yl) Substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole
Beilstein Journal of Organic Chemistry. 2014. V.10. P.1596-1602. DOI: 10.3762/bjoc.10.165 WOS Scopus OpenAlex

Submitted:	Mar 30, 2014
Accepted:	Jun 16, 2014
Published print:	Jul 14, 2014
Published online:	Jul 14, 2014

Web of science:	WOS:000338956300001
Scopus:	2-s2.0-84904546759
OpenAlex:	W2138333382

DB	Citing
Scopus	34
OpenAlex	29
Web of science	35