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

Mammadova F., Ozsinan S., Okutan M., DENGİZ Ç.

Journal of Molecular Structure, cilt.1220, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1220
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.molstruc.2020.128726
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Donor-acceptor systems, Nonlinear optics, Charge transfer, Conjugation, Cycloaddition, Solvatochromism, 2+2 CYCLOADDITION-RETROELECTROCYCLIZATION, CHARGE-TRANSFER INTERACTIONS, DONOR-ACCEPTOR CHROMOPHORES, RAY CRYSTAL-STRUCTURES, 7,7,8,8-TETRACYANOQUINODIMETHANE TCNQ, SMALL MOLECULES, SPIRO SYSTEMS, COMPLEXES, RUTHENIUM, CHEMISTRY
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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 hyper-polarizability 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. (C) 2020 Elsevier B.V. All rights reserved.