An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes

Gonzalo Anguera; Won-Young Cha; Matthew D Moore; James T Brewster 2nd; Michael Y Zhao; Vincent D Lynch; Dongho Kim; Jonathan L Sessler

doi:10.1002/anie.201711197

An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes

Angew Chem Int Ed Engl. 2018 Mar 1;57(10):2575-2579. doi: 10.1002/anie.201711197. Epub 2018 Jan 16.

Authors

Gonzalo Anguera¹, Won-Young Cha², Matthew D Moore¹, James T Brewster 2nd^{1

3}, Michael Y Zhao¹, Vincent D Lynch¹, Dongho Kim², Jonathan L Sessler^{1

3}

Affiliations

¹ Department of Chemistry, The University of Texas at Austin, 105 East 24th Street, Stop A5300, Austin, TX, 78712-1224, USA.
² Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 03722, Korea.
³ Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai, 200444, China.

PMID: 29314606
DOI: 10.1002/anie.201711197

Abstract

A new expanded porphycene with 26 π-electrons has been prepared by the McMurry coupling of 1,4-bis(3,4-diethyl-2-pyrryl)benzene dialdehyde. Expansion of the porphycene framework provides a ligand capable of stabilizing a bis(rhodium) and a monoruthenium complex. These new porphycene derivatives absorb strongly in the NIR spectral region, with appreciable absorptivity up to 1300 nm. On the basis of their ground- and excited-state spectroscopic features and structural parameters, both the free-base system and the bis(rhodium) complex are considered to be Hückel-type aromatic systems. This conclusion is supported by DFT calculations.

Keywords: McMurry reaction; macrocycles; near-infrared absorption; porphycenes; rhodium.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't