Synthesis, characterization of novel cyclohexenone derivatives and computation of their optical response Amir Badshah a , Muhammad Faizan Nazar b,⇑ , Asif Mahmood c , Waqas Ahmed d , Muhammad Imran Abdullah e , Muhammad Naveed Zafar b , Usman Ali Rana f a Institute of Chemical Sciences, University of Peshawar, Pakistan b Department of Chemistry, University of Gujrat, Gujrat, Pakistan c Department of Chemistry, University of Sargodha, Sargodha, Pakistan d Office of Research, Innovation and Commercialization, University of Gujrat, Pakistan e Institute of Chemistry, University of the Punjab, Lahore, Pakistan f Deanship of Scientific Research, College of Engineering, King Saud University, Riyadh, Saudi Arabia highlights  A viable approach for the synthesis of five new cyclohexenone derivatives from Robinson annulation is described.  Micro- and spectral analysis have been effectively operated to confirm the molecular structures of cyclohexenones.  As-synthesized cyclohexenones exhibit intense violet fluorescence and display high hyperpolarizability values.  The computed and experimental electronic transitions are in good agreement. graphical abstract article info Article history: Received 18 February 2014 Received in revised form 24 April 2014 Accepted 24 April 2014 Available online 6 May 2014 Keywords: Cyclohexenones Fluorescence Polarizability Hyperpolarizability TD-DFT NLO abstract The present study reports the successful development of five new cyclohexenone derivatives (CDs) using rational design synthesis principles and quantum chemical calculations. These new CDs were synthesized by following a convenient route of Robinson annulation, and the molecular structure of these CDs were later confirmed by various analytical techniques such as 1 H NMR, 13 C NMR, FT-IR, UV–Vis spectroscopy and Mass spectrometry. The results from spectroscopic studies show that the as-synthesized CDs mole- cules apparently emit violet light at about 406–414 nm. Moreover, polarizability (a) and first static hyperpolarizability (b) were computed by density functional theory (DFT). In addition, the UV–Vis spec- tra, transition character and electronic structures of these CDs were computed by using the time depen- dent density functional theory (TD-DFT). It was interesting to note that the values of computed and experimental electronic transitions (k max ) were in good agreement. Finally, the measurements of higher non-linear optical (NLO) response of our newly synthesized CDs suggest their potential for application in photonic devices. Ó 2014 Elsevier B.V. All rights reserved. Introduction At present, the developments of materials that exhibit second- order nonlinear optical (NLO) responses are receiving significant http://dx.doi.org/10.1016/j.molstruc.2014.04.074 0022-2860/Ó 2014 Elsevier B.V. All rights reserved. ⇑ Corresponding author. Address: Office # 12, Department of Chemistry, Institute of Chemical and Biological Sciences, University of Gujrat, Gujrat-50700, Pakistan. Tel.: +92 3016942411; fax: +92 533643167. E-mail addresses: faizan_qau@yahoo.com, faizan.nazar@uog.edu.pk (M.F. Nazar). Journal of Molecular Structure 1071 (2014) 103–110 Contents lists available at ScienceDirect Journal of Molecular Structure journal homepage: www.elsevier.com/locate/molstruc