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Effects of Intra- and Intermolecular Hydrogen Bonding on O–H Bond Photodissociation Pathways of a Catechol Derivative

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. A 2019, 123, 25, 5356-5366
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    Effects of Intra- and Intermolecular Hydrogen Bonding on O–H Bond Photodissociation Pathways of a Catechol Derivative
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    • Christopher Grieco
      Christopher Grieco
      Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States
      More by Christopher Grieco
    • Alex T. Hanes
      Alex T. Hanes
      Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States
      More by Alex T. Hanes
    • Lluís Blancafort*
      Lluís Blancafort
      Institut de Química Computacional i Catàlisi and Departament de Química, Facultat de Ciències, Universitat de Girona, C/M.A. Capmany 69, 17003 Girona, Spain
      *E-mail: [email protected] (L.B.).
      More by Lluís Blancafort
      Orcidhttp://orcid.org/0000-0002-0003-5540
    • Bern Kohler*
      Bern Kohler
      Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States
      *E-mail: [email protected] (B.K.).
      More by Bern Kohler
      Orcidhttp://orcid.org/0000-0001-5353-1655
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2019, 123, 25, 5356–5366
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    https://doi.org/10.1021/acs.jpca.9b04573
    Published June 27, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    The catechol functional motif is thought to play both a structural and photochemical role in the ubiquitous natural pigment, eumelanin. Intramolecular and intermolecular hydrogen bonding interactions lead to a variety of geometries involving the two O–H groups in catechol, but its photophysical behavior in these situations has not been comprehensively characterized. Toward this end, we monitor the UV-induced O–H bond photodissociation reaction in an exemplar catechol derivative, 4-tert-butylcatechol, possessing different intramolecular and intermolecular hydrogen bonding geometries using femtosecond transient absorption spectroscopy measurements in the UV–visible and mid-infrared regions following 265 nm photoexcitation. Three different hydrogen bonding arrangements are obtained by tuning solution complexation equilibria of the catechol with the hydrogen bond acceptor, diethyl ether (Et2O), and are verified computationally. We find that intermolecular hydrogen bonding to the free O–H group in catechol increases its first excited singlet state (S1) lifetime by 2 orders of magnitude (i.e., ∼ 16 to 1410 ps), and that O–H bond dissociation is prevented because Et2O is a poor hydrogen atom acceptor. Complexation of both O–H groups with multiple Et2O molecules further elongates the S1 lifetime to 1670 ps due to shifting of the solution equilibria that describe complex formation. Weakening of the characteristic, intramolecular hydrogen bond of the catechol derivative by intermolecular hydrogen bonding to one or more Et2O molecules does not enhance the rate of O–H bond dissociation.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpca.9b04573.

    • Scheme showing all structures in Table 1, additional transient absorption spectra and kinetics, TRIR analysis, FTIR analysis, UV irradiation results, and computational details (PDF)

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    Cited By

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    This article is cited by 16 publications.

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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2019, 123, 25, 5356–5366
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpca.9b04573
    Published June 27, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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