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Article

Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations

1
Micron School of Materials Science and Engineering, Boise State University, Boise, ID 83725, USA
2
Department of Electrical and Computer Engineering, Boise State University, Boise, ID 83725, USA
3
Department of Chemistry and Biochemistry, Boise State University, Boise, ID 83725, USA
4
Center for Advanced Energy Studies, Idaho Falls, ID 83401, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Jose C. Corchado
Molecules 2021, 26(3), 524; https://doi.org/10.3390/molecules26030524
Received: 8 December 2020 / Revised: 11 January 2021 / Accepted: 15 January 2021 / Published: 20 January 2021
(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Physical Chemistry)
The aggregation ability and exciton dynamics of dyes are largely affected by properties of the dye monomers. To facilitate aggregation and improve excitonic function, dyes can be engineered with substituents to exhibit optimal key properties, such as hydrophobicity, static dipole moment differences, and transition dipole moments. To determine how electron donating (D) and electron withdrawing (W) substituents impact the solvation, static dipole moments, and transition dipole moments of the pentamethine indocyanine dye Cy5, density functional theory (DFT) and time-dependent (TD-) DFT calculations were performed. The inclusion of substituents had large effects on the solvation energy of Cy5, with pairs of withdrawing substituents (W-W pairs) exhibiting the most negative solvation energies, suggesting dyes with W-W pairs are more soluble than others. With respect to pristine Cy5, the transition dipole moment was relatively unaffected upon substitution while numerous W-W pairs and pairs of donating and withdrawing substituents (D-W pairs) enhanced the static dipole difference. The increase in static dipole difference was correlated with an increase in the magnitude of the sum of the Hammett constants of the substituents on the dye. The results of this study provide insight into how specific substituents affect Cy5 monomers and which pairs can be used to engineer dyes with desired properties. View Full-Text
Keywords: density functional theory; time dependent density functional theory; cyanine dye; Cy5; exciton; solubility; dipole moment density functional theory; time dependent density functional theory; cyanine dye; Cy5; exciton; solubility; dipole moment
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MDPI and ACS Style

Biaggne, A.; Knowlton, W.B.; Yurke, B.; Lee, J.; Li, L. Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations. Molecules 2021, 26, 524. https://doi.org/10.3390/molecules26030524

AMA Style

Biaggne A, Knowlton WB, Yurke B, Lee J, Li L. Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations. Molecules. 2021; 26(3):524. https://doi.org/10.3390/molecules26030524

Chicago/Turabian Style

Biaggne, Austin, William B. Knowlton, Bernard Yurke, Jeunghoon Lee, and Lan Li. 2021. "Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations" Molecules 26, no. 3: 524. https://doi.org/10.3390/molecules26030524

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