Synthesis, spectroscopic characterization, and computed optical analysis of green fluorescent cyclohexenone derivatives. (6th November 2015)

• Record Type: Journal Article
• Authors: Nazar, Muhammad Faizan; Badshah, Amir; Mahmood, Asif; Zafar, Muhammad Naveed; Janjua, Muhammad Ramzan Saeed Ashraf; Raza, Muhammad Asam; Hussain, Riaz
• Is Part Of: Journal of physical organic chemistry. Volume 29:Number 3(2016)
• Page Start: 152
• Page End: 160
• Publication Date: 2015-11-06
• Subjects: crystallizability -- cyclohexenones -- fluorescent -- hyperpolarizability -- nonlinear optical; Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3512
• Languages: English
• ISSNs: 0894-3230

Abstract

Abstract: Cyclohexenone containing chalcones core is one important class of materials, which exhibit high nonlinear optical (NLO) responses and good crystallizability. The present study reports the successful development of six new fluorescent cyclohexenone derivatives (CDs) via conventionalRobinson annulation method. The molecular structures of these newly synthesized CDs were confirmed by using variousanalytical techniques such as 1 H NMR, 13 C NMR, FTIR, EIMS, UV–Vis spectroscopy and single crystal X‐ray diffraction. The crystallographic data revealed that the spatial structure of the representative CD (4BE) belongs to monoclinic, P21 /c space group. The results from luminescence studies show that the CDs molecules apparently emit intense green light at room temperature in aqueous media. The relative polarity and molecularchemical stability of the CDs molecules were predicted by measuring the molecular electrostatic potential and frontier molecular orbital energy. In addition, the UV–Vis spectra, transition character and electronic structures of these CDs were computed by using quantum chemical methodology. It was interesting to note that the values of computed and experimental electronic transitions (λmax ) were in good agreement and these CDs display high hyperpolarizability ( β ) values. The present work will be helpful for systematical understanding of the structures and the optical properties of CDs for studying thestructure–activity relationship that will suggest their potential application inphotonic devices . Copyright © 2015 John Wiley & Sons, Ltd. Abstract : Six new cyclohexenone derivatives were synthesized via Robinson annulations method and their molecular structures were confirmed by elemental and spectral analyses. Chemically oriented electronic structures of as‐synthesized cyclohexenones displayed potential nonlinear optical properties and exhibit intense green fluorescence. The quantum chemical calculations were found consonant with the experimental results.