[5]helicene-fused phthalocyanine derivatives. New members of the phthalocyanine family

Thanasat Sooksimuang; Braja K Mandal

doi:10.1021/jo026413v

[5]helicene-fused phthalocyanine derivatives. New members of the phthalocyanine family

J Org Chem. 2003 Jan 24;68(2):652-5. doi: 10.1021/jo026413v.

Authors

Thanasat Sooksimuang¹, Braja K Mandal

Affiliation

¹ Department of Biological, Chemical, and Physical Sciences, Illinois Institute of Technology, 3255 S. Dearborn Street, Chicago 60616, USA.

PMID: 12530905
DOI: 10.1021/jo026413v

Abstract

An efficient synthetic route to fuse [5]helicene moieties around the phthalocyanine core is reported. The helicene moiety was constructed by the Diels-Alder reaction of 3,4,3',4'-tetrahydro-1,1'-dinaphthyl and dibromobenzyne. Subsequent cyanation, oxidation, O-alkylation, and cyclic tetramerization resulted in octaalkoxy phthalocyanine derivatives which showed high solubility in common organic solvents and displayed strong absorption in the near-IR region.