The Influence of the Isosteric Exchange of Benzene by Thiophene-Core of Phthalocyanine: The Synthesis, Structure and Opto-Electronic Behavior of π-Conjugated Unit Blocks in Materials

Abstract

The strategy of isosteric replacement of the benzene ring with a thiophene core was applied in the design of phthalocyanine 1 with the aim for reaching an effective organic chromophore as employable content in organic photovoltaic devices. The formation of the desired product was not achieved but the approach created organic small-molecules 2 and 3. These, representing the reactive intermediates, were converted to novel hemiphthalocyanine 4. Although undesired, all exhibit absorbance in the visible region (λ_max ~ 400 nm) and proximity of the HOMO/LUMO band edge (E_g: 2.0–3.5 eV), suggesting that compounds 2–4 behaves as an effective π-conjugated linkers in donor-π-acceptor type dyes for dye sensitized solar cells and related high performing energetic devices.