1 Supporting Information meso-Aryl tribenzosubporphyrin – A totally substituted subporphyrin species Elena A. Makarova, a Soji Shimizu, b Atsushi Matsuda, b Evgeny A. Lu’kyanets, ＊ a and Nagao Kobayashi ＊ b Organic Intermediates and Dyes Institute, B. Sadovaya 1/4, Moscow, 123995, Russia and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan 1. Experimental General procedure Electronic absorption spectra were recorded with Hitachi U-3410 and JASCO V-570 spectrophotometers. Magnetic circular dichroism (MCD) spectra were recorded with a JASCO J-725 spectrodichrometer equipped with a JASCO electromagnet, which produces magnetic fields of up to 1.09 T (1T = 1 tesla) with both parallel and antiparallel fields. The magnitudes were expressed in terms of molar ellipticity per tesla ([q] M / deg dm 3 mol -1 cm -1 T -1 ). Fluorescence spectrum was measured with a Hitachi F-4500 spectrofluorimeter with appropriate filters installed to eliminate scattered light. 1 H and 13 C NMR spectra, and 1 H- 1 H and 13 C- 1 H two dimensional spectra were recorded on a JEOL ECA-600 spectrometer (operating as 594.17 MHz for 1 H and 149.40 MHz for 13 C) using the residual solvent as the internal reference for 1 H (δ = 5.320 ppm for CD 2 Cl 2 ), and 13 C (δ = 53.1 ppm for CD 2 Cl 2 ). High resolution mass spectra of 2-OH and 2-OEt were recorded on a Bruker Daltonics Apex-III spectrometer. X-ray crystallographic studies were carried out on a Rigaku Saturn CCD spectrometer with graphite monochromatized Mo Kα radiation (λ = 0.71073 Å). The structures were derived using the SHELXS-97 program and refined on F 2 using the SHELXL-97 program. [1] CV and DPV measurements were recorded on a Hokuto Denko HZ5000 potentiostat under argon in o-dichlorobenzene (DCB) solutions with tetrabutylammonium perchlorate (TBAP, 0.1 M) as the supporting electrolyte. Measurements were carried out with a glassy carbon electrode (area = 0.07 cm 2 ), an Ag/AgCl reference electrode, and a Pt wire counter-electrode. The concentration of the solution was fixed at 0.5 mM and the sweep rates were 100 mV/s and 10mV/s for CV and DPV measurements, respectively. The ferrocene/ferrocenium (Fc/Fc + ) couple was used as internal standard. The Gaussian03 software package [2] was used to carry out DFT and TDDFT calculations using the B3LYP functional with 6-31G(d) basis sets. [3] Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008