Facile and versatile access to substituted hexabenzoovalene derivatives: characterization and optoelectronic properties?

Organic & Biomolecular Chemistry Pub Date: 2019-08-01 DOI: 10.1039/C9OB01446B

Abstract

We describe the design and modular synthesis of a library of substituted hexabenzoovalene derivatives (SHBO), along with the key precursor dinaphthopyrenes (3), highlighting the influence of a wide array of substituent variation on the photophysical properties via UV-vis absorption, fluorescence spectra and electrochemical methods. The results show that the cyclized hexabenzoovalenes present a stronger spectroscopic red-shift than the corresponding dinaphthopyrenes. X-ray diffraction analysis suggests that intermediate 3hx containing two nitro groups forms a trans-configuration with twisted structures. Our systematic investigation might provide a realistic design strategy to construct large one-dimensional and two-dimensional materials via bottom-up approaches.

Graphical abstract: Facile and versatile access to substituted hexabenzoovalene derivatives: characterization and optoelectronic properties
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