Cyanobuta-1,3-dienes as novel electron acceptors for photoactive multicomponent systems

Chemistry : a European Journal
Francesca TanciniFrançois Diederich

Abstract

The synthesis, electrochemical, and photophysical properties of five multicomponent systems featuring a Zn(II) porphyrin (ZnP) linked to one or two anilino donor-substituted pentacyano- (PCBD) or tetracyanobuta-1,3-dienes (TCBD), with and without an interchromophoric bridging spacer (S), are reported: ZnP-S-PCBD (1), ZnP-S-TCBD (2), ZnP-TCBD (3), ZnP-(S-PCBD)2 (4), and ZnP-(S-TCBD)2 (5). By means of steady-state and time-resolved absorption and luminescence spectroscopy (RT and 77 K), photoinduced intramolecular energy and electron transfer processes are evidenced, upon excitation of the porphyrin unit. In systems equipped with the strongest acceptor PCBD and the spacer (1, 4), no evidence of electron transfer is found in toluene, suggesting ZnP→PCBD energy transfer, followed by ultrafast (<10 ps) intrinsic deactivation of the PCBD moiety. In the analogous systems with the weaker acceptor TCBD (2, 5), photoinduced electron transfer occurs in benzonitrile, generating a charge-separated (CS) state lasting 2.3 μs. Such a long lifetime, in light of the high Gibbs free energy for charge recombination (ΔG(CR)=-1.39 eV), suggests a back-electron transfer process occurring in the so-called Marcus inverted region. Notably, in system 3 l...Continue Reading

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Citations

Oct 9, 2015·The Journal of Physical Chemistry. a·Filippo MontiNicola Armaroli
Mar 4, 2017·Chemistry : a European Journal·Tristan A ReekieFrançois Diederich
Aug 9, 2017·Chemistry : a European Journal·Taku Shoji, Shunji Ito
Feb 28, 2020·Chemical Communications : Chem Comm·Anh Thy BuiYann Trolez
Feb 1, 2018·The Journal of Organic Chemistry·Alberto Viñas MuñozMogens Brøndsted Nielsen
Sep 30, 2021·Physical Chemistry Chemical Physics : PCCP·Nicolas RipocheFrédéric Paul

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