Phthalocyanine Monolayers Self-Assembled Directly from its Thiobenzoyl Derivative

Thiol- and thioacetate-based functional groups enjoy much attention as anchors for building of self-assembled monolayers (SAM), while SAM formation based on readily accessible benzoyl derivatives remain unexploited. In the present work, we study the SAM-forming ability of a simple octylthiobenzoate and a redox-active metal-free phthalocyanine bearing two thiobenzoyl-terminated diethyleneglycol chains. By the means of cyclic voltammetry for both solutions and SAMs of the studied phthalocyanine compound, it was demonstrated that this anchoring group does indeed allow formation of densely packed SAMs from the thiobenzoyl-containing compounds on gold surface without the need in additional ex situ deprotection synthetic step. This approach could be used for further design of novel building blocks for SAM containing this anchor group.