Encapsulation of TCNQ and the acridinium ion within a bisporphyrin cavity: synthesis, structure, and photophysical and HOMO-LUMO-gap-mediated electron-transfer properties

Chemistry : a European Journal
Arvind Chaudhary, Sankar Prasad Rath

Abstract

The encapsulation of tetracyanoquinodimethane (TCNQ) and fluorescent probe acridinium ions (AcH(+)) by diethylpyrrole-bridged bisporphyrin (H(4)DEP) was used to investigate the structural and spectroscopic changes within the bisporphyrin cavity upon substrate binding. X-ray diffraction studies of the bisporphyrin host (H(4)DEP) and the encapsulated host-guest complexes (H(4)DEP⋅TCNQ and [H(4)DEP⋅AcH]ClO(4)) are reported. Negative and positive shifts of the reduction and oxidation potentials, respectively, indicated that it was difficult to reduce/oxidize the encapsulated complexes. The emission intensities of bisporphyrin, upon excitation at 560 nm, were quenched by about 65 % and 95 % in H(4)DEP⋅TCNQ and [H(4)DEP⋅AcH]ClO(4), respectively, owing to photoinduced electron transfer from the excited state of the bisporphyrin to TCNQ/AcH(+); this result was also supported by DFT calculations. Moreover, the fluorescence intensity of encapsulated AcH(+) (excited at 340 nm) was also remarkably quenched compared to the free ions, owing to photoinduced singlet-to-singlet energy transfer from AcH(+) to bisporphyrin. Thus, AcH(+) acted as both an acceptor and a donor, depending on which part of the chromophore was excited in the host-guest...Continue Reading

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Citations

Jan 12, 2016·The Journal of Physical Chemistry. a·Li-Li WangHai-Yang Liu
Mar 18, 2016·Inorganic Chemistry·Soumyajit DeySankar Prasad Rath
Jan 6, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Firoz Shah Tuglak KhanSankar Prasad Rath
May 31, 2017·Chemistry : a European Journal·Tapas GuchhaitSankar Prasad Rath
May 4, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Dipti LaiSankar Prasad Rath
Aug 11, 2015·Chemical Communications : Chem Comm·Sk Asif IkbalSankar Prasad Rath
Jul 15, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Debangsu Sil, Sankar Prasad Rath
Sep 25, 2017·Chemistry : a European Journal·Philipp Lang, Matthias Schwalbe
Aug 25, 2016·Chemistry : a European Journal·Debangsu SilSankar Prasad Rath
Jul 17, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Avinash DhamijaSankar Prasad Rath
Mar 31, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Dipali N LandeShridhar P Gejji
Jul 13, 2017·Chemistry : a European Journal·Younis Ahmad PanditSankar Prasad Rath
Jan 6, 2021·ChemPlusChem·Henri-Pierre Jacquot de RouvilleValérie Heitz
Sep 4, 2020·Angewandte Chemie·Johnny HuHenri-Pierre Jacquot de Rouville

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