An Anthracene-Incorporated [8]Cycloparaphenylene Derivative as an Emitter in Photon Upconversion

J Org Chem. 2018 Jan 5;83(1):220-227. doi: 10.1021/acs.joc.7b02590. Epub 2017 Dec 26.

Abstract

The anthracene-incorporated [8]cycloparaphenylene 2 has been synthesized and its optoelectronic properties studied by UV-vis spectroscopy, cyclic voltammetry, and DFT calculations. NMR and computational studies indicate that the new cycloparaphenylene derivative possesses a Cs point group symmetry. The new CPP 2 exhibits peculiar optoelectronic properties: (i) fluorescence emission is blue-shifted with respect to [8]cycloparaphenylene 1, and its quantum yield is higher; (ii) in the presence of an octaethylporphyrin Pd complex, as sensitizer, it undergoes a visible light upconversion. This is the first case in which a cycloparaphenylene derivative is involved as an emitter in low power light frequency conversion.

Publication types

  • Research Support, Non-U.S. Gov't