Air- and Water-Stable, Fluorescent Oligomers of 9,10-Dihydro-9,10-diboraanthracene

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• 作者：Christian Reus ; Fang Guo ; Alexandra John ; Marcel Winhold ; Hans-Wolfram Lerner ; Frieder J盲kle ; Matthias Wagner
• 刊名：Macromolecules
• 出版年：2014
• 出版时间：June 10, 2014
• 年：2014
• 卷：47
• 期：11
• 页码：3727-3735
• 全文大小：488K
• 年卷期：v.47,no.11(June 10, 2014)
• ISSN：1520-5835

文摘

Air- and water-stable, 蟺-conjugated [鈭抎onor鈥揳cceptor鈭抅_n oligomers containing thiophene fragments as donors and 9,10-dimesityl-9,10-dihydro-9,10-diboraanthracene (DBA(Mes)₂) as acceptor units were prepared through Stille-type C鈥揅-coupling protocols. The reaction between 2,6-dibromo-DBA(Mes)₂ (1), 2,7-dibromo-DBA(Mes)₂ (2), 2-bromo-6,7-dimethyl-DBA(Mes)₂ (3), and 2,5-bis(trimethylstannyl)thiophene (7) furnished monodisperse, short-chain model systems 8₀ (2 脳 DBA(Mes)₂, 1 脳 2,5-thienylene) and 8₁ (3 脳 DBA(Mes)₂, 2 脳 2,5-thienylene) after GPC separation. In the absence of 3, the oligomerization of 1/2 with 7 provided analogous longer chain macromolecules 9 (MALDI鈥揗S reveals up to 7 repeating units; GPC indicates also significantly longer chains). UV/vis absorption spectroscopy suggests that the obtained chain lengths of 9 are already sufficient to reach the maximum effective conjugation length (the lower limit of the HOMO鈥揕UMO band gap corresponds to 2.3 eV). 9 gives rise to a dark orange fluorescence, both in C₆H₆ solution (_f = 47%) and as thin film (_f = 13%).