Photophysical properties of a boron analogue of coumarin

Huayi Wang; Briana R. Schrage; Kana Takematsu; Christopher J. Ziegler

doi:10.1039/d1cp02386a

Photophysical properties of a boron analogue of coumarin

Huayi Wang, Briana R. Schrage, Kana Takematsu, Christopher J. Ziegler

Research output: Contribution to journal › Article › peer-review

Abstract

In this report, we present a study into the structure and electronic properties of difluoroboronsalicylaldoxime (DFBS), a boron-based structural analog of coumarin. The modification of the heterocyclic ring of coumarin with boron results in a compound with similar structural parameters and molecular orbitals to coumarin. DFT and TDDFT calculations reveal a significant stabilization of the LUMO in DFBS; this is supported by a ∼40 nm red shift of the lowest electronic transition in the absorption spectrum. Interestingly, DFBS is emissive, while unmodified coumarin is effectively non-radiative. Comparisons between DFBS, emissive coumarin variants, and unmodified coumarin suggest that the charge transfer character of the transition contributes to the fluorescence.

Original language	English
Pages (from-to)	18855-18862
Number of pages	8
Journal	Physical Chemistry Chemical Physics
Volume	23
Issue number	34
DOIs	https://doi.org/10.1039/d1cp02386a
State	Published - Sep 14 2021
Externally published	Yes

Funding

K. T. would like to acknowledge Bowdoin College and Research Corporation for Science Advancement (Cottrell Scholar Award) for support of this work.

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title = "Photophysical properties of a boron analogue of coumarin",

abstract = "In this report, we present a study into the structure and electronic properties of difluoroboronsalicylaldoxime (DFBS), a boron-based structural analog of coumarin. The modification of the heterocyclic ring of coumarin with boron results in a compound with similar structural parameters and molecular orbitals to coumarin. DFT and TDDFT calculations reveal a significant stabilization of the LUMO in DFBS; this is supported by a ∼40 nm red shift of the lowest electronic transition in the absorption spectrum. Interestingly, DFBS is emissive, while unmodified coumarin is effectively non-radiative. Comparisons between DFBS, emissive coumarin variants, and unmodified coumarin suggest that the charge transfer character of the transition contributes to the fluorescence.",

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T1 - Photophysical properties of a boron analogue of coumarin

AU - Wang, Huayi

AU - Schrage, Briana R.

AU - Takematsu, Kana

AU - Ziegler, Christopher J.

PY - 2021/9/14

Y1 - 2021/9/14

N2 - In this report, we present a study into the structure and electronic properties of difluoroboronsalicylaldoxime (DFBS), a boron-based structural analog of coumarin. The modification of the heterocyclic ring of coumarin with boron results in a compound with similar structural parameters and molecular orbitals to coumarin. DFT and TDDFT calculations reveal a significant stabilization of the LUMO in DFBS; this is supported by a ∼40 nm red shift of the lowest electronic transition in the absorption spectrum. Interestingly, DFBS is emissive, while unmodified coumarin is effectively non-radiative. Comparisons between DFBS, emissive coumarin variants, and unmodified coumarin suggest that the charge transfer character of the transition contributes to the fluorescence.

AB - In this report, we present a study into the structure and electronic properties of difluoroboronsalicylaldoxime (DFBS), a boron-based structural analog of coumarin. The modification of the heterocyclic ring of coumarin with boron results in a compound with similar structural parameters and molecular orbitals to coumarin. DFT and TDDFT calculations reveal a significant stabilization of the LUMO in DFBS; this is supported by a ∼40 nm red shift of the lowest electronic transition in the absorption spectrum. Interestingly, DFBS is emissive, while unmodified coumarin is effectively non-radiative. Comparisons between DFBS, emissive coumarin variants, and unmodified coumarin suggest that the charge transfer character of the transition contributes to the fluorescence.

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DO - 10.1039/d1cp02386a

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VL - 23

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EP - 18862

JO - Physical Chemistry Chemical Physics

JF - Physical Chemistry Chemical Physics

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ER -

Photophysical properties of a boron analogue of coumarin

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