Self-organization of a new fluorous porphyrin and C60 films on indium-tin-oxide electrode

Abstract

The highly fluorinated alkyl moieties of a new porphyrin drive the self-organization of thin films with C60 on ITO electrodes.

Microcrystals engineering using assemblies of di-protonated meso-tetraphenylporphine dimers under Zundel cations operation

“…In this connection dimerization of metal free TPP in aqueous-organic solutions in the presence of HCl represents a special interest because it involves Zundel ions in the cage between TPP in a dimer, while alternatively not ionized TPP species were aggregated and precipitated from a solution [21]. Earlier it has been established that H 5 ";, which is the same as that for TPP in dioxane without a counterion, indicates not only a large hydration of the dimer but also perhaps an expulsion of the chloride anion from the cage of the dimer. In contrast, the excitation energy for the aminoporphyrin dimers that is within 1.72-1.60 eV, i.e.…”

“…Self-organization and self-assembly of different supramolecular structures are of major interest in different fields of research and scanning probe microscopy revealed new views [1][2][3][4][5][6]. Hydrogen bonding, p-p interactions, and cooperative effects play an important role in the self-organizing and self-assembling processes.…”

Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

“…In their protocol, the porphyrin and the thiol are treated at room temperature in a mixture of ethyl acetate and DMF with a dialkylamine derivative as base. [21,22] In all five cases, a solution of TPPF 20 in DMF was added to a solution of the thiol (i.e., 9, 14, 16, 19, or 20; 6.0-10.0 equiv.) and diethylamine in a mixture of ethyl acetate and DMF.…”

“…This para-fluorine substitution reaction in pentafluorophenyl moieties is not limited to porphyrin systems. [12][13][14] The first example for the fourfold substitution reaction of TPPF 20 with a nucleophile was reported by Kadish et al [15] Examples with non-fluorous alcohols, [16][17][18] amines, [16,17] or thiols [16,19] as well as the introduction of fluorous nucleophiles -namely alcohols [20] and thiols [21,22] are also known.…”

Introduction

“…Fluorinated porphyrin derivatives which were further derivatized with perfluoro alkyl chains as well as fullerene (C 60 ) were used to prepare self-assembled thin films on an indium-tin-oxide electrode. This new nanomaterial is remarkably stable, being robust to oxidative damage, if used as a film on surfaces (16); it can be used for solar energy conversion and energy storage, because the complexes can form long-lived charge-separated states.…”