C3-Symmetric star shaped donor–acceptor truxenes: synthesis and photophysical, electrochemical and computational studies

Autor:	Rekha Sharma, Rajneesh Misra, Ramesh Maragani
Rok vydání:	2018
Předmět:	010405 organic chemistry Chemistry Sonogashira coupling General Chemistry Star (graph theory) 010402 general chemistry Photochemistry Electrochemistry 01 natural sciences Acceptor Catalysis 0104 chemical sciences Materials Chemistry Donor acceptor
Zdroj:	New Journal of Chemistry. 42:882-890
ISSN:	1369-9261 1144-0546
DOI:	10.1039/c7nj03934d
Popis:	This manuscript reports the design and synthesis of C3-symmetric star shaped donor and acceptor substituted truxenes 6, 7, 10 and 11 using Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition–retroelectrocyclization reactions. Their photophysical, electrochemical and computational studies were explored, which indicate strong donor–acceptor interactions and effective tuning of the HOMO–LUMO gap. The computational studies reveal that the TCNE and TCNQ substituted truxenes 10 and 11 exhibit lower HOMO–LUMO gaps compared to truxenes 6 and 7. The reaction pathway of [2+2] cycloaddition–retroelectrocyclization was studied using computational calculations, which reveal that the donor substituted truxene 7 is favourable for cycloaddition–retroelectrocyclization reactions, whereas acceptor substituted truxene 6 is not favourable.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5cd0992da5315f829e140d9ac3e930bc https://doi.org/10.1039/c7nj03934d Zobrazit plný text záznamu