Synthesis, characterization, and theoretical investigation of optical and nonlinear optical (NLO) properties of triazene-based push–pull chromophores

Date

2020-11-15

Author

Mammadova, Flora
Ozsinan, Semin
Okutan, Merve
Dengiz, Çağatay

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A short and efficient synthetic strategy for the synthesis of triazene-substituted push–pull dyes has been developed. The formal [2 + 2] cycloaddition-retroelectrocyclization was utilized for the preparation of the target push–pull dyes. These atom-economic, click-type chemical transformations occurred under ambient conditions and provided structurally interesting push–pull dyes in high yields. The effects of different triazene substituents on optical and non-linear optical properties were investigated by means of density functional theory (DFT), in order to support design criteria. The dipole moment, HOMO-LUMO gaps, electronegativity, global chemical hardness and softness, average polarizability, first hyperpolarizability were calculated for push–pull dyes at the CAM-B3LYP/6–31++G(d,p) level of theory. Frontier orbital depictions and electrostatic potential maps were used to establish charge-transfer characteristics of the aforementioned molecules.

Subject Keywords

Inorganic Chemistry, Organic Chemistry, Analytical Chemistry, Spectroscopy, Donor-acceptor systems, Nonlinear optics, Charge transfer, Conjugation, Cycloaddition, Solvatochromism

URI

https://hdl.handle.net/11511/42076

Journal

Journal of Molecular Structure

DOI

https://doi.org/10.1016/j.molstruc.2020.128726

Collections

Department of Chemistry, Article

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Citation Formats

F. Mammadova, S. Ozsinan, M. Okutan, and Ç. Dengiz, “Synthesis, characterization, and theoretical investigation of optical and nonlinear optical (NLO) properties of triazene-based push–pull chromophores,” Journal of Molecular Structure, pp. 0–0, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42076.