Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations.
Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations.
复制标题
对氰染料CY5的溶解性和电子特性的取代效应：密度功能和时间依赖性密度功能理论计算。
DOI：
10.3390/molecules26030524
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发表时间：
2021-01-20
期刊：
影响因子：
--
通讯作者：
Li L
中科院分区：
文献类型：
--
作者：
Biaggne A;Knowlton WB;Yurke B;Lee J;Li L
染料的聚集能力和激子动力学很大程度上受染料单体性质的影响。为了促进聚集和改善激子功能，可以用取代基对染料进行改造，使其具有最佳的关键性质，如疏水性、静态偶极矩差和跃迁偶极矩。用密度泛函理论(DFT)和含时密度泛函(TD-)方法计算了给电子取代基(D)和吸电子取代基(W)对五甲胺吲哚菁染料Cy5的溶剂化、静态偶极矩和跃迁偶极矩的影响.取代基的加入对Cy5的溶剂化能有较大影响，其中W-W对的负溶剂化能最大，说明W-W对的染料比其他对的染料更易溶解。对于原始的Cy5，取代对跃迁偶极矩的影响相对较小，而大量的W-W对和给予和退出取代对(D-W对)增强了静态偶极差。静态偶极差的增加与染料上取代基的Hammett常数之和的大小有关。这项研究的结果为深入了解特定取代基如何影响Cy5单体以及哪些对可以用于设计具有所需性能的染料提供了深入的了解。
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.
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影响因子：
16.6
作者：
Bialas, David;Zitzler-Kunkel, Andre;Kirchner, Eva;Schmidt, David;Wuerthner, Frank
通讯作者：
Wuerthner, Frank
DOI：
10.1039/c7cp08549d
发表时间：
2018-03-28
期刊：
Physical chemistry chemical physics : PCCP
影响因子：
--
作者：
Heid E ;Hunt PA ;Schröder C
通讯作者：
Schröder C
影响因子：
2.9
作者：
Bamgbelu, Anu;Wang, Jing;Leszczynski, Jerzy
通讯作者：
Leszczynski, Jerzy
影响因子：
2.3
作者：
Abramavicius D;Palmieri B;Mukamel S
通讯作者：
Mukamel S
影响因子：
5.7
作者：
Huff, Jonathan S.;Davis, Paul H.;Pensack, Ryan D.
通讯作者：
Pensack, Ryan D.