Appending Diverse π-Extended Acceptors with Tetrathiafulvalene/Dithiafulvalene Donors: Multistate Redox Properties, Radical Ion Generation, and Mid-IR-Absorbing Mixed-Valence States

Chemistry : a European Journal
Sudhir Kumar KeshriPritam Mukhopadhyay

Abstract

Three classes of donor-acceptor (D-A) π-extended chromophores (1-12) were synthesized through a phosphite-mediated cross-coupling reaction, in which the anhydride- or imide-based π-As and number of tetrathiafulvalene (TTF)/dithiafulvalene (DTF) Ds were systematically changed. Large π rings, such as benzoperylene and coronene, were integrated into the TTF/DTF unit, for the first time, to overcome their high insolubility. The anhydride and imide groups in the π acceptors can significantly alter the frontier orbitals and influence the optoelectronic properties. The D moieties allow the formation of radical cations (D.+) and the π-extended A moieties aid the formation of radical anions (A.-) by oxidation/reduction under ambient conditions. The molecules revealed UV/Vis/near-IR absorption, fluorescence extending into the near-IR region, and amphoteric electrochemical properties. Chromophores 10 and 12 show solvatochromism in a wide range of solvents. The π-As with anhydride functionality allow easier electron uptake, relative to the imide groups, whereas the increasing number of D TTF/DTF units make them easy to oxidize. Interestingly, the trans-TTF-fused molecules (1, 6, and 11) exhibited a mixed-valence state in the mid-IR region ...Continue Reading

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Citations

Jul 24, 2018·Chemistry : a European Journal·Hiroko YamadaNaoki Aratani
Feb 1, 2019·Chemistry : a European Journal·Sharvan KumarPritam Mukhopadhyay
Mar 11, 2020·ChemistryOpen·Jyoti ShuklaPritam Mukhopadhyay
Feb 5, 2021·Chemistry : a European Journal·Sudhir Kumar KeshriPritam Mukhopadhyay
Apr 1, 2020·Journal of the American Chemical Society·Kang CaiJ Fraser Stoddart

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