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Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno-Fused π-Expanded Fluorenes and Their Characterization
, Jagarapu R., Maddala S., Mahto I.
Published in John Wiley & Sons, Inc.
Volume: 9
Issue: 12
Pages: 2144 - 2152
Differently-linked bithienyl-attached fluorenes have been synthesized. While the oxidative photodicyclization of 2,3′-bithiophene-containing fluorene was successful to yield tetrathieno-fused regioisomeric π-expanded fluorenes, the reaction with 2,2′-bithiophene-containing fluorene was very sluggish. Interestingly, the connectivity in bithiophenes appears to determine the (photo)reactivity. On the one hand, under mild Scholl conditions, 2,3′-bithiophene-containing fluorene yielded a highly regioselective product while 2,2′-bithiophene-containing fluorene led to polymerization. The optical and electrochemical properties of tetrathienoannulated π-expanded fluorenes were investigated, and they were found to be quite different from those of the phenanthreno-annulated π-expanded analogues. These newly obtained sulfur-edged π-expanded fluorenes may hold promise in organic electronics. © 2020 Wiley-VCH GmbH
About the journal
JournalData powered by TypesetAsian Journal of Organic Chemistry
PublisherData powered by TypesetJohn Wiley & Sons, Inc.
Open AccessNo