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Synthesis, spectroscopic characterization, and computed optical analysis of green fluorescent cyclohexenone derivatives
Author(s) -
Nazar Muhammad Faizan,
Badshah Amir,
Mahmood Asif,
Zafar Muhammad Naveed,
Janjua Muhammad Ramzan Saeed Ashraf,
Raza Muhammad Asam,
Hussain Riaz
Publication year - 2016
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3512
Subject(s) - chemistry , hyperpolarizability , cyclohexenone , monoclinic crystal system , molecular orbital , homo/lumo , molecule , carbon 13 nmr , proton nmr , luminescence , spectroscopy , fluorescence , crystallography , chemical physics , crystal structure , optoelectronics , stereochemistry , optics , organic chemistry , materials science , physics , quantum mechanics , polarizability
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 conventional Robinson annulation method. The molecular structures of these newly synthesized CDs were confirmed by using various analytical 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, P2 1 /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 molecular chemical 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 (λ max ) 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 the structure–activity relationship that will suggest their potential application in photonic devices . Copyright © 2015 John Wiley & Sons, Ltd.