TY - JOUR A1 - Kostyuchenko, Anastasia S. A1 - L.Yurpalov, Vyacheslav A1 - Kurowska, Aleksandra A1 - Domagala, Wojciech A1 - Pron, Adam A1 - Fisyuk, Alexander S. T1 - 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 JF - Beilstein Journal of Organic Chemistry PY - 2014/// VL - 10 SP - 1596 EP - 1602 SN - 1860-5397 DO - 10.3762/bjoc.10.165 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.10.165 KW - bithiophene KW - donor–acceptor KW - luminescence KW - 1,3,4-oxadiazole KW - 1,3,4-thiadiazole KW - 4H-1,2,4-triazole N2 - 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. ER -