Synthesis of Fused Chalcogenophenocarbazoles: Towards Dual Emission Resulting from Hybridized Local and Charge-Transfer States

New Journal of Chemistry 2020
Alla Petrenko, Oleksandr Bezvikonnyi, Dmytro Volyniuk, Yan Danyliv, Jurate Simokaitiene, Sergejs Beļakovs, Juozas Vidas Gražulevičius, Pavel Arsenyan

Fused chalcogenophenocarbazoles bearing a trimethylsilylpropyl substituent at the nitrogen atom of carbazole were synthesized starting with 2,7-dibromocarbazole by subsequent alkylation, iodination at positions 3 and 6, Sonogashira coupling and, finally, creation of thiophene and selenophene rings. Depending on the heteroatom and its charge, the compounds were characterized by fluorescence resulting from recombination of either locally excited, intramolecular charge-transfer or hybridized local and charge-transfer (HLCT) states. This is the first report on dual emission of HLCT character observed for chalcogenophenocarbazoles.

Keywords
versatile synthesis; thiophene; benzothiophenes; derivatives; annulation; efficient; pyrrole
DOI
10.1039/c9nj06211d
Hyperlink
https://pubs.rsc.org/en/content/articlelanding/2020/NJ/C9NJ06211D#!divAbstract

Petrenko, A., Bezvikonnyi, O., Volyniuk, D., Danyliv, Y., Simokaitiene, J., Beļakovs, S., Gražulevičius, J., Arsenyan, P. Synthesis of Fused Chalcogenophenocarbazoles: Towards Dual Emission Resulting from Hybridized Local and Charge-Transfer States. New Journal of Chemistry, 2020, Vol. 44, No. 10, pp.3903-3911. ISSN 1144-0546. e-ISSN 1369-9261. Available from: doi:10.1039/c9nj06211d

Publication language
English (en)