Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
Abstract
:1. Introduction
2. Results and Discussion
2.1. Photo-Induced Hydrogen Bonding Strengthening
2.2. Vertical Excitation
2.3. ESDPT Behaviors
3. Computational Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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BBTHQ-SO | BBTHQ-SS | BBTHQ-SSe | ||||
---|---|---|---|---|---|---|
S0 | S1 | S0 | S1 | S0 | S1 | |
O1-H2 | 0.98488 | 1.01016 | 0.98858 | 1.02371 | 0.98914 | 1.02617 |
H2⋯N3 | 1.80813 | 1.68964 | 1.75430 | 1.61607 | 1.74982 | 1.60720 |
O4-H5 | 0.98870 | 1.02551 | 0.98858 | 1.02371 | 0.98865 | 1.02306 |
H5⋯N6 | 1.75141 | 1.60963 | 1.75430 | 1.61607 | 1.75384 | 1.61770 |
Δ(O1H2N3) | 145.17 | 148.19 | 146.01 | 149.76 | 146.14 | 150.03 |
Δ(O4H5N6) | 146.04 | 150.09 | 146.01 | 149.76 | 146.01 | 149.71 |
BBTHQ-SO | BBTHQ-SS | BBTHQ-SSe | |||||
---|---|---|---|---|---|---|---|
S0 | S1 | S0 | S1 | S0 | S1 | ||
O1-H2⋯N3 | ELF(C-V,D) | 0.0993 | 0.1010 | 0.1010 | 0.1035 | 0.1011 | 0.1038 |
ELF(DH-A) | 0.1592 | 0.2240 | 0.1888 | 0.2826 | 0.1932 | 0.2929 | |
CVB index | −0.0599 | −0.1230 | −0.0878 | −0.1791 | −0.0921 | −0.1891 | |
O4-H5⋯N6 | ELF(C-V,D) | 0.1010 | 0.1036 | 0.1010 | 0.1035 | 0.1010 | 0.1034 |
ELF(DH-A) | 0.1901 | 0.2876 | 0.1888 | 0.2826 | 0.1891 | 0.2811 | |
CVB index | −0.0891 | −0.1840 | −0.0878 | −0.1791 | −0.0881 | −0.1777 |
Mulliken’s Charge | NPA Charge | ||||
---|---|---|---|---|---|
Atoms | S0 | S1 | S0 | S1 | |
BBTHQ-SO | O1 | −0.282 | −0.276 | −0.652 | −0.650 |
H2 | 0.297 | 0.297 | 0.505 | 0.503 | |
N3 | −0.148 | −0.151 | −0.492 | −0.496 | |
O4 | −0.283 | −0.279 | −0.653 | −0.651 | |
H5 | 0.305 | 0.305 | 0.502 | 0.497 | |
N6 | −0.109 | −0.121 | −0.471 | −0.477 | |
BBTHQ-SS | O1 | −0.284 | −0.280 | −0.654 | −0.652 |
H2 | 0.304 | 0.305 | 0.503 | 0.497 | |
N3 | −0.112 | −0.123 | −0.471 | −0.478 | |
O4 | −0.284 | −0.280 | −0.654 | −0.652 | |
H5 | 0.304 | 0.305 | 0.503 | 0.497 | |
N6 | −0.112 | −0.123 | −0.471 | −0.478 | |
BBTHQ-SSe | O1 | −0.284 | −0.280 | −0.654 | −0.653 |
H2 | 0.305 | 0.305 | 0.503 | 0.497 | |
N3 | −0.122 | −0.135 | −0.471 | −0.479 | |
O4 | −0.285 | −0.280 | −0.653 | −0.652 | |
H5 | 0.304 | 0.304 | 0.502 | 0.496 | |
N6 | −0.113 | −0.124 | −0.478 | −0.485 |
BBTHQ-SO | BBTHQ-SS | BBTHQ-SSe | |
---|---|---|---|
A → C | 3.5574 | 1.8323 | 1.5976 |
C → D | 1.9277 | 1.9971 | 2.0237 |
A → B | 1.7520 | 1.8323 | 1.9976 |
B → D | 3.8121 | 1.9971 | 1.7131 |
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Zhao, J.; Liu, C. Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone. Molecules 2023, 28, 5951. https://doi.org/10.3390/molecules28165951
Zhao J, Liu C. Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone. Molecules. 2023; 28(16):5951. https://doi.org/10.3390/molecules28165951
Chicago/Turabian StyleZhao, Jinfeng, and Chang Liu. 2023. "Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone" Molecules 28, no. 16: 5951. https://doi.org/10.3390/molecules28165951