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Substituent effects on the UV–visible spectrum and excited electronic states of dithiocarboxylates

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Abstract

The absorption spectra of a series of dithiocarboxylates were investigated in the ultraviolet–visible region. Two questions that this study aimed to address were as follows: (1) What transitions give rise to the features in the electronic spectra? And (2) what are the long- and short-range substituent effects on the absorption spectra? A series of 11 dithiocarboxylates were prepared as organic soluble salts. Time-dependent density functional theory (TDDFT) was used to calculate excited state energies and oscillator strengths of electronic transitions. TDDFT at the CAM-B3LYP/def2-TZVPD level of theory predicts two low-energy n → π* transitions and two π → π* transitions at higher energy, consistent with the experimental spectra. This state ordering and density is in contrast to the better studied thiocarbonyls for which only two transitions within the singlet manifold appear in the UV–visible region. For derivatives of dithiobenzoate, the energy of the three lowest energy states are insensitive to changes to substituents para to the dithiocarboxylate group. In contrast, the energy of the highest ππ* state varies by 0.78 eV. This work shows that the results of TDDFT calculations can be used to predict the electronic absorption spectra of dithiocarboxylates, providing a useful tool for designing dithiocarboxylate light absorbers.

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Acknowledgements

We thank The Frost Fund (https://cosam.calpoly.edu/frost-fund) for supporting this research with the purchase of a UV–visible Spectrophotometer, and for funding summer research supplies and stipends. Start-up funds from the Cal Poly College of Science and Mathematics were also used to support this research. We also thank undergraduate students whose contributions to other projects supported the group success: Mark Mattison (B.S. 2018), Terrace Wong (B.S. 2019), Jonathan Richarte, Micah McClure (B.S. 2021), Kiely Payne (Templeton H.S. 2019), Henry Mull (B.S. 2019), Nicholas Baird, Erik McCutchen, An Pham, and Monica Aichouri. DFZ thanks Dr. Megan Grabenauer of RTI, International for editorial discussions during preparation of the manuscript.

Funding

The work herein was financially supported by The Frost Fund (https://cosam.calpoly.edu/frost-fund) and with start-up funds from the Cal Poly College of Science and Mathematics

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  1. Jose P. Madriaga

    Present address: Department of Chemistry, Virginia Tech, Blacksburg, VA, 24060, USA

  2. J. Michael Sieffert

    Present address: Department of Chemistry, McGill University, Montreal, QC, H3A0G4, Canada

  3. Shannon E. Heinrich

    Present address: Department of Chemistry, University of California, Santa Barbara, CA, 93106, USA

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  1. Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Ave., San Luis Obispo, CA, 93405, USA

    Abraham K. Newman, Ava M. Henry, Jose P. Madriaga, J. Michael Sieffert, Shannon E. Heinrich, Juliana T. Jarboe, Vincent M. Swift, Alicia Y. Y. Cheong, M. Taylor Haynes & David F. Zigler

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43630_2021_144_MOESM1_ESM.docx

Supplementary file1 The Supporting Information document contains additional experimental details and results organized into sections as follows: all experimental procedures (Section S1), comparative experimental and theoretical absorbance spectra for each compound (Section S2), natural transition orbitals (Section S3.1), theoretical electronic state transition assignments (Section S3.2), characterization data (Appendix A1-A3), and coordinates of optimized structures (Appendix A4) (DOCX 9139 KB)

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Newman, A.K., Henry, A.M., Madriaga, J.P. et al. Substituent effects on the UV–visible spectrum and excited electronic states of dithiocarboxylates. Photochem Photobiol Sci 21, 303–318 (2022). https://doi.org/10.1007/s43630-021-00144-5

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