Toward Prediction of Nonradiative Decay Pathways in Organic Compounds II: Two Internal Conversion Channels in BODIPYs

Lin, Zhou; Kohn, Alexander W.; Van Voorhis, Troy

doi:10.1021/acs.jpcc.9b08292

Cited by 78Luminescence and Fluorescent MaterialsPhotochemistry and Electron Transfer StudiesAdvanced Chemical Physics Studies

Toward Prediction of Nonradiative Decay Pathways in Organic Compounds II: Two Internal Conversion Channels in BODIPYs

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Lin, Zhou, Kohn, Alexander W., Van Voorhis, Troy·2020·The Journal of Physical Chemistry C

DOI 10.1021/acs.jpcc.9b08292

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Abstract

Boron-dipyrromethene (BODIPY) molecules are widely used as laser dyes and have therefore become a popular research topic within recent years. Numerous studies have been reported for the rational design of BODIPY derivatives based on their photophysical properties, including absorption and fluorescence wavelengths (λ abs and λ fl ), oscillator strength ( f ), nonradiative pathways, and quantum yield (Φ). In the present work, we illustrate a theoretical, semiempirical model that accurately predicts Φ for various BODIPY compounds on the basis of inexpensive electronic structure calculations, following the data-driven algorithm proposed by us in a previous study [Kohn et al. J. Phys. Chem. C. 2019, 123, 15394]. The model allows us to identify the dominant nonradiative channel of any BODIPY molecule using its structure exclusively and to establish a correlation between the activation energy ( E a ) and the fluorescence quantum yield (Φ fl ). On the basis of our calculations, either the S 1 → S 0 or L a → L b internal conversion (IC) mechanism dominates in the majority of BODIPY derivatives, depending on the structural and electronic properties of the substituents. In either case, the nonradiative rate ( k nr ) exhibits a straightforward Arrhenius-like relation with the associated E a . More interestingly, the S 1 → S 0 mechanism proceeds via a highly distorted intermediate structure in which the core BODIPY plane and the substituent at the 1-position are twisted, while the internal rotation of the very same substituent induces the L a → L b transition. Our model reproduces k fl, k nr, and Φ fl to mean absolute errors (MAEs) of 0.16 decades, 0.87 decades, and 0.26, when all outliers are considered. These results allow us to validate the predictive power of the proposed data-driven algorithm in Φ fl . They also indicate that the model has a great potential to facilitate and accelerate the machine learning aided design of BODIPY dyes for imaging and sensing applications, given sufficient experimental data and appropriate molecular descriptors.

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The current paradigm in photochemistry points out that nonradiative deactivation from the excited-state molecules involves a conical intersection (CI).
“The current paradigm in photochemistry (unreasonably overlooked in the materials science community) points out that nonradiative deactivation from the excited-state molecules involves a conical intersection (CI).134−139”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [139]
The magnitude of vibronic interactions approaches infinity at the CI, where the S1 and S0 degenerate, from which the excitons decay nonradiatively.
“The magnitude of vibronic interactions approaches infinity at the CI, where the S1 and S0 degenerate, from which the excitons decay nonradiatively.”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [139]

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Authors: Lin, Z., Kohn, A. W., & Van Voorhis, T.
Affiliations: Massachusetts Institute of Technology (US)
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States
ORCID: Lin, Zhou
Kohn, Alexander W.
Van Voorhis, Troy
Venue: The Journal of Physical Chemistry C
Publisher: American Chemical Society (ACS)
Published: 2020-01-20
Volume: 124
Issue: 7
Pages: 3925-3938
ISSN: 1932-7447 (ISSN-L)
1932-7455
DOI: 10.1021/acs.jpcc.9b08292
OpenAlex: W3001474577
Cited by: 78
References: 155
Citations by year: 2026: 6 · 2025: 10 · 2024: 7 · 2023: 12 · 2022: 14 · 2021: 21 · 2020: 8
FWCI: 5.34
Type: journal article
Language: en
Open access: green
doi.org
Licence: cc-by-nc-nd
doi.org/10.15223/policy-029 (stm-asf)
doi.org/10.15223/policy-037 (stm-asf)
doi.org/10.15223/policy-045 (stm-asf)
Locations: The Journal of Physical Chemistry C (publishedVersion)
ChemRxiv (acceptedVersion, cc-by-nc-nd)
DSpace@MIT (Massachusetts Institute of Technology) (submittedVersion, cc-by-nc-sa)
Figshare (submittedVersion, cc-by-nc-nd)
Funders: Basic Energy Sciences (DE-FG02-07ER46474)
Topics: Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
Physical Sciences › Physics and Astronomy › Atomic and Molecular Physics, and Optics › Advanced Chemical Physics Studies
Keywords: BODIPY, nonradiative decay, fluorescence quantum yield, internal conversion, S1-S0 transition, triplet state, activation energy, data-driven prediction models, semi-empirical model, molecular twisting, laser dyes

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Toward Prediction of Nonradiative Decay Pathways in Organic Compounds II: Two Internal Conversion Channels in BODIPYs

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