Through-space π-delocalization in a conjugated macrocycle consisting of [2.2]paracyclophane?

Chemical Communications Pub Date: 2019-11-11 DOI: 10.1039/C9CC06492C

Abstract

Herein, we report the synthesis and characterization of a [2.2]paracyclophane-containing macrocycle (PCMC) as a new through-space conjugated macrocycle using only benzene groups as the skeleton. For comparison, a diphenylmethane-containing nanohoop macrocycle (DCMC) with a non-conjugated linker was also synthesized. Their structures were confirmed by NMR and HR-MS, and their photophysical properties were studied by UV-vis and fluorescence spectroscopies combined with theoretical calculations. The strain energy of PCMC was estimated to be as high as 72.58 kcal mol?1.

Graphical abstract: Through-space π-delocalization in a conjugated macrocycle consisting of [2.2]paracyclophane
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