HETEROCYCLES

■ Synthesis of Long-Wavelength Absorbing Porphyrin m-Benzoic Acids as Molecular Tectons for Surface Studies

Alina Meindl, Aoife A. Ryan, Keith J. Flanagan, and Mathias O. Senge*

*Medicinal Chemistry, Trinity Centre for Health Sciences, Trinity College Dublin, St. James's Hospital, Dublin 8, Ireland

Abstract

Porphyrins are becoming increasingly important building blocks in material science. This is due in part to several favorable characteristics; such as strong absorption into the infrared region, tunable electronic properties and the possibility to modify and define the porphyrin core in multiple ways. Herein we report synthetic methodologies for porphyrin-based molecular tectons for surface studies. The study aims to generate porphyrins with directional anchoring groups of different length and we report a library of long-wavelength absorbing porphyrins with a special focus on organometallic coupling reactions for the introduction of benzoic acid moieties as anchor groups.