Abstract
Novel scaffolds of indenofluorene (IF)-extended tetrathiafulvalenes (TTF) were synthesized starting from a new pyrrolo-annelated IF-TTF monomer. Rigid para- and meta-phenylene linked dimers were obtained via N-arylation reactions of the monomer, and their optical and redox properties were elucidated by UV-Vis absorption spectroscopy and cyclic and differential pulse voltammetries.
Highlights
Novel scaffolds of indenofluorene (IF)-extended tetrathiafulvalenes (TTF) were synthesized starting from a new pyrrolo-annelated IF-TTF monomer
X-Ray crystallographic and computational studies reveal that all three redox states (0, +1, +2), generated in sequential and reversible steps, take a fully planar structure, and spectroelectrochemical studies have shown that the individual redox states exhibit signi cantly redshi ed absorptions relative to those of TTF, TTF+, and TTF2+, respectively.[2]
Prepared cis/trans isomeric IF-TTF dimers had exible linkers and showed intramolecular associations upon oxidation,[4] which would be prevented by these rigid linkers
Summary
Novel scaffolds of indenofluorene (IF)-extended tetrathiafulvalenes (TTF) were synthesized starting from a new pyrrolo-annelated IF-TTF monomer. Tetrathiafulvalene (TTF) is a redox-active unit that reversibly undergoes two sequential one-electron oxidations, forming rst a radical cation (TTF+) and subsequently a dication (TTF2+) containing two aromatic 1,3-dithiolium rings, and it is due to these redox properties that it is an attractive unit for materials and supramolecular chemistries.[1] This procedure, previously applied for N-arylation of pyrrolo-annelated TTFs,[6] yielded dimers 2 and 3, respectively.
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