Malaysian Journal of Analytical Sciences Vol 26 No 4 (2022): 684 - 697

 

 

 

 

SYNTHESIS, PHOTOPHYSICAL AND COMPUTATIONAL APPROACHES ON NONLINEAR OPTICAL (NLO) PROPERTIES OF NAPHTHALEN-1-YL ETHYNYLATED-CHALCONE DERIVATIVE

 

(Sintesis, Pendekatan Fotofizik dan Pengkomputeran Terhadap Sifat Optik Tak Linear (NLO) bagi Terbitan Naftalen-1-il Teretinil-Kalkon)

 

Mas Mohammed¹, Wan M. Khairul¹*, Rafizah Rahamathullah², Fazira Ilyana Abdul Razak³, Suhaila Sapari⁴

 

¹Faculty of Science and Marine Environment,

Universiti Malaysia Terengganu, 21030, Kuala Nerus, Terengganu, Malaysia

²Faculty of Engineering Technology,

Universiti Malaysia Perlis, Level 1, Blok S2, Kampus UniCITI Alam, Sungai Chuchuh, 02100, Perlis, Malaysia

³Department of Chemistry, Faculty of Science,

Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

⁴Department of Chemical Sciences, Faculty Science and Technology,

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia.

 

*Corresponding author:  wmkhairul@umt.edu.my

 

 

Received:  10 March 2022; Accepted:  23 April 2022; Published:  25 August 2022

 

 

Abstract

A new dual mixed moieties of acetylide (C C) and chalcone (-CO-CH=CH) system namely 3-(naphthalen-1-yl)-1-(4-(phenylethynyl)phenyl)-2-propen-1-one (3NPP) was successfully designed and synthesized via Claisen Schmidt condensation reacti on. Spectroscopic characterization and thermal analysis were conducted via Infrared Spectroscopy (FTIR), ¹H and ¹³C Nuclear Magnetic Resonance (NMR) and Thermogravimetric (TGA) analysis. Density functional theory (DFT) assessment with basis set of B3LYP/6-31G (d,p) was computed to investigate the energy level of HOMO and LUMO, charge transfer within the molecule by global chemical reactivity descriptors (GCRD), molecular electrostatic potentials (MEP) and hyperpolarizability analyses. The simulated calculation reveals that the HOMO-LUMO energy gap of 3NPP exhibited at 3.51 eV and has demonstrated good agreement with experimental optical band gap (E_g^opt). Additionally, 3NPP possesses high NLO response with total first hyperpolarizability ( _tot) of 420.51  10^-30 esu. The presence of π-conjugated acetylide groups has improved nonlinear optical property and potential for application in optoelectronic.

 

Keywords:  ethynyl, chalcone, density functional theory, non-linear optics, first hyperpolarizability

 

Abstrak

Moiti dwi tercampur sistem asetilida (C≡C) dan kalkon (-CO-CH=CH) baharu yang diberi nama 3-(naftalen-1-il)-1-((4-feniletinil)fenil)-2-propen-1-on (3NPP) telah berjaya direkabentuk dan disintesis melalui tindak balas kondensasi Claisen Schmidt. Pencirian spektroskopi dan analisis terma telah dijalankan melalui spektroskopi inframerah (FTIR), ¹H dan ¹³C Resonan Magnetik Nuklear (NMR) dan analisis termogravimetrik (TGA). Penilaian fungsi teori ketumpatan (DFT) dengan set asas B3LYP/6-31G (d,p) telah dikira untuk mengkaji jurang tenaga bagi HOMO dan LUMO, pemindahan caj dalam sebatian melalui petunjuk kereaktifan kimia global (GCRD), potensi elektrostatik molekul (MEP) dan analisis hiperpolarisasi. Pengiraan simulasi menunjukkan jurang tenaga HOMO-LUMO 3NPP memberikan nilai 3.51 eV dan ternyata menunjukkan nilai yang selari dengan jurang tenaga optik eksperimen (E_g^opt). Tambahan pula, 3NPP mempunyai sifat NLO yang tinggi dengan jumlah hiperpolarisasi pertama (β_tot) sebanyak 420.51x 10^-30 esu. Dengan kehadiran kumpulan asetilida π-terkonjugat telah meningkatkan sifat optik tak linear dan berpotensi untuk aplikasi optoelektronik.

 

Kata kunci:  etinil, kalkon, fungsi teori ketumpatan, sifat optik tak linear, hiperpolarisasi pertama

 

Graphical Abstract

 

 

 

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