Influence of substituents on the vectorial difference static dipole upon excitation in synthetic bacteriochlorins

Ketteridge, Maia N.; Watt, Devan R.; Duncan, Katelyn M.; Barcenas, German; Shaw, Kaden; Knowlton, William B.; Yurke, Bernard; Pensack, Ryan D.; Mass, Olga A.; Li, Lan

doi:10.1021/acs.jpca.4c03821

Influence of substituents on the vectorial difference static dipole upon excitation in synthetic bacteriochlorins

Journal Article · Mon Jan 01 00:00:00 EST 2024 · The Journal of Physical Chemistry

DOI:https://doi.org/10.1021/acs.jpca.4c03821· OSTI ID:2434305

^[1]; Watt, Devan R. ^[2]; ^[2]; ^[2]; Shaw, Kaden ^[3]; ^[4]; ^[4]; ^[2]; ^[2]; ^[5]

Micron School of Materials Science and Engineering, Boise State University, Boise, ID 83725, USA; Boise State University
Micron School of Materials Science and Engineering, Boise State University, Boise, ID 83725, USA
Brigham Young University, Idaho, Rexburg, ID 83460, USA
Micron School of Materials Science and Engineering, Boise State University, Boise, ID 83725, USA; Department of Electrical and Computer Engineering, Boise State University, Boise, ID 83725, USA
Micron School of Materials Science and Engineering, Boise State University, Boise, ID 83725, USA; Center for Advanced Energy Studies, Idaho Falls, ID 83401, USA

Organic dye aggregates have been shown to exhibit exciton delocalization in natural and synthetic systems. Such dye aggregates show promise in the emerging area of quantum information science (QIS). We believe that the difference static dipole (Δd) is an essential dye parameter in the development of molecular QIS systems. However, a foundational understanding of the structural factors influencing Δd remains elusive. Bacteriochlorins play a vital role in photosynthesis due to their exceptional photophysical properties. Therefore, bacteriochlorins are particularly suitable dyes for the construction of aggregate systems for QIS. Synthetic bacteriochlorins further offer stability and tunability via chemical modifications. Here, the influence of substituents on the Δd of monomeric (non-aggregated) dyes was investigated via density functional theory (DFT) and time-dependent (TD-)DFT in a set of 5-methoxybacteriochlorins progressively substituted with ethynyl, phenyl, and phenylethynyl substituents at the 3,13- and 3,13,15-positions of the macrocycle. Symmetrically substituted 5-methoxybacteriochlorins were shown to have the largest Δd. The increase in Δd in the series of dyes was largely due to changes in orientation of the static dipole upon excitation rather than large changes in magnitude. In addition, the transition dipole (μ) and the angle between Δd and μ (ζ) were calculated. Three 5-methoxybacteriochlorins with high predicted Δd and μ were synthesized and characterized spectroscopically. The trend in Δd values empirically determined using the solvatochromic Stokes shift method was comparable with the DFT calculations.

View Accepted Manuscript (DOE)

Research Organization:: Boise State University

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0020089

OSTI ID:: 2434305

Journal Information:: The Journal of Physical Chemistry, Journal Name: The Journal of Physical Chemistry; ISSN 1089-5639

Country of Publication:: United States

Language:: English

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Influence of substituents on the vectorial difference static dipole upon excitation in synthetic bacteriochlorins

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