Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

Autor: Sven M. Elbert, Tobias Kirschbaum, Frank Rominger, Michael Mastalerz
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Organic Materials, Vol 03, Iss 02, Pp 097-102 (2021)
Druh dokumentu: article
ISSN: 2625-1825
DOI: 10.1055/s-0041-1726304
Popis: Abstract Homoconjugation is a phenomenon discussed for various π-systems where classical conjugation is broken by e.g. methylene units but still a stabilization by electronic communication exists. In this respect, triptycene with its rigid C3 symmetric geometry is an ideal scaffold to study this phenomenon. Although several studies based on triptycene strengthen the hypothesis of homoconjugation, in all described cases the electronic communication through space relies on different π-blades. Here, two triptycenes are presented having the exact same π-extended chromophore, but differently annulated to the bicyclic core. Both compounds were investigated by spectroscopic as well as computational means and compared with the corresponding model compound, elucidating the influence of the attachment site to the triptycene core on potential homoconjugation.
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