Photoinduced hole injection into a self-assembled π-extended G-quadruplex

Journal of the American Chemical Society
Yi-Lin WuMichael R Wasielewski

Abstract

We have prepared a G-quadruplex (GQ-1) that incorporates an 8-(4'-aminophenylethynyl)guanine (GEAn) electron donor covalently attached to a 4-aminonaphthalene-1,8-imide (ANI) chromophore and a naphthalene-1,8:4,5-bis(dicarboximide) (NDI) electron acceptor (GEAn-ANI-NDI, 1). In the presence of KPF6 in tetrahydrofuran (THF), 1 self-assembles into a monodisperse, C4-symmetric GQ-1 with small spatial intraquadruplex overlap between the ANI-NDI units. Photoexcitation of monomeric 1 induces the two-step charge transfer GEAn-(1)*ANI-NDI → GEAn(+•)-ANI(-•)-NDI → GEAn(+•)-ANI-NDI(-•) that occurs in τ(CS1) = 5 ps and τ(CS2) = 330 ps, respectively, while charge recombination in ca. 300 ns. Sharpening of the GEAn(+•) transient absorption and a shift of the ethynyl vibrational frequency in 1 were observed, concomitant with the stepwise electron transfer from ANI(-•) to NDI. Formation of GQ-1 from 1 in THF increases the secondary charge-shifting rate (τ(CS2) = 110 ps) and results in no change in ethynyl vibrational frequency. Charge recombination in GQ-1 is slowed by enhanced radical-pair intersystem crossing driven by the greater number of hyperfine couplings in the assembly. Moreover, time-resolved EPR spectroscopy shows that the spin-spin...Continue Reading

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Citations

Apr 16, 2016·Journal of the American Chemical Society·Michelle A HarrisFrederick D Lewis
Jan 18, 2017·Journal of the American Chemical Society·Arun K ThazhathveetilFrederick D Lewis
Jan 20, 2017·Organic Letters·Elham FadaeiDavid González-Rodríguez
Jan 25, 2018·Faraday Discussions·Kristen E BrownMichael R Wasielewski
Jul 6, 2016·Chemical Communications : Chem Comm·Miguel García-IglesiasDavid González-Rodríguez
Mar 4, 2020·Angewandte Chemie·Miguel Martín-ArroyoDavid González-Rodríguez
Apr 22, 2017·Nature Chemistry·Yi-Lin WuMichael R Wasielewski
Apr 8, 2020·ChemistryOpen·Anselmo Del PradoYi-Lin Wu
Dec 3, 2020·The Journal of Chemical Physics·Natalia E Powers-RiggsMichael R Wasielewski
Jun 17, 2021·Chemical Reviews·Meera MadhuMahesh Hariharan
Jun 8, 2021·Chemistry : a European Journal·Nicolás M CasellasMiguel García-Iglesias
Aug 3, 2018·Accounts of Chemical Research·Frederick D LewisMichael R Wasielewski
Oct 28, 2019·Journal of the American Chemical Society·Natalia E Powers-RiggsMichael R Wasielewski
Aug 3, 2017·Journal of the American Chemical Society·Kristen E BrownMichael R Wasielewski
Sep 17, 2020·The Journal of Physical Chemistry. a·Branislav MilovanovićMihajlo Etinski

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