title: 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.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russia ; Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, Omsk 644050, Russia.
authors.forename: Anastasia S
authors.initials: AS
authors.lastname: Kostyuchenko
authors.affiliation: Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russia.
authors.forename: Vyacheslav
authors.initials: V
authors.lastname: L Yurpalov
authors.affiliation: Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Kurowska
authors.affiliation: Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland.
authors.forename: Wojciech
authors.initials: W
authors.lastname: Domagala
authors.affiliation: Faculty of Chemistry Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland.
authors.forename: Adam
authors.initials: A
authors.lastname: Pron
authors.affiliation: Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russia ; Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, Omsk 644050, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Fisyuk
keywords: 1,3,4-oxadiazole; 1,3,4-thiadiazole; 4H-1,2,4-triazole; bithiophene; donor–acceptor; luminescence