N-annulated perylene fused porphyrins with enhanced near-IR absorption and emission

Chongjun Jiao; Kuo-Wei Huang; Zhenping Guan; Qing-Hua Xu; Jishan Wu

doi:10.1021/ol1016383

N-annulated perylene fused porphyrins with enhanced near-IR absorption and emission

Org Lett. 2010 Sep 17;12(18):4046-9. doi: 10.1021/ol1016383.

Authors

Chongjun Jiao¹, Kuo-Wei Huang, Zhenping Guan, Qing-Hua Xu, Jishan Wu

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore.

PMID: 20734983
DOI: 10.1021/ol1016383

Abstract

N-Annulated perylene fused porphyrins 1 and 2 were synthesized by oxidative dehydrogenation using a Sc(OTf)(3)/DDQ system. These newly synthesized hybrid molecules are highly soluble in organic solvents and exhibit remarkably intense near-IR absorption, as well as detectable photoluminescence quantum yields, all of which are comparable to or even exceed those of either meso-β doubly linked porphyrin dimer/trimer or bis/tri-N-annulated rylenes.

Publication types

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

MeSH terms

Models, Molecular
Molecular Structure
Oxidation-Reduction
Perylene / chemistry*
Porphyrins / chemistry*
Spectrophotometry, Infrared

Substances

Porphyrins
Perylene