Malaysian Journal of Analytical Sciences, Vol 27 No 1 (2023): 96 - 107

THE EFFECT OF ANTHRACENE GROUP SUBSTITUTION OF DISUBSTITUTED CHALCONE DERIVATIVE FEATURING TEREPHTHALALDEHYDE π-LINKER ON NON-LINEAR OPTICAL (NLO) CHARACTERISTIC

(Kesan Penggantian Kumpulan Antrasena Atas Terbitan Kalkon Dualgantian Yang Menampilkan Terephthalaldehid π-Penyambung Keatas Ciri-Ciri Optik Bukan Linear)

Nurul Nabilah Shuaib¹, Adibah Izzati Daud^1*, Suhana Arshad², Mohamad Aizat Abu Bakar³, Wan M. Khairul⁴

¹Faculty of Engineering and Chemical Technology,

Universiti Malaysia Perlis,

02600 Arau, Perlis, Malaysia.

²School of Physics,

Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia.

³Institute of Nano Optoelectronics Research and Technology (INOR),

Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

⁴Faculty of Science and Marine Environment,

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

^*Corresponding author: adizzati@unimap.edu.my

Received: 22 September 2022; Accepted: 17 January 2023; Published: 22 February 2023

Abstract

In past years, the π-conjugated system has attracted much attention as a promising material for developing and manufacturing the next generation of organic electronics made of synthesised organic compounds. Chalcone, having the π-conjugated systems in their molecular structures and the unique α, β-unsaturated ketone structural, have gained much attraction due to their potential use in optoelectronics applications like organic light emitting diode (OLED). By altering the molecular structure, the physical and chemical properties of chalcone derivatives can be tailored to the application needed. In recent years, chemists have produced many types of π-conjugated molecules to acquire excellent luminescence characteristics from organic compounds, and such structures typically lead to intense colour and excellent photoluminescence. In this study, a disubstituted chalcone derivative featuring terephthalaldehyde (N1A) as a π-linker with anthracene as donating group substitution has been synthesised through the Claisen-Schmidt condensation reaction. The synthesised compound has been characterised using Fourier Transform Infrared spectroscopy (FTIR) and UV-Visible analysis. Density functional theory (DFT) computations are executed to evaluate the effect of anthracene as an electron donating substitution on NLO properties of disubstituted chalcone derivative. NLO responses of this disubstituted chalcone derivative disclose that the chalcone molecular framework exhibit an important characteristic for further application as OLED emitting material.

Keywords: chalcone, density functional theory, non-linear optical, spectroscopic

Abstrak

Pada tahun-tahun lepas, sistem π-konjugasi telah menarik banyak perhatian sebagai bahan yang berpotensi untuk dibangunkan dan dikeluarkan sebagai generasi seterusnya elektronik organik, yang dibuat daripada sintesis sebatian organik. Kalkon, yang mempunyai sistem terkonjugasi-π dalam struktur molekulnya serta struktur keton α, β-tak tepu yang unik, telah mendapat banyak tarikan kerana potensi penggunaannya dalam aplikasi optoelektronik seperti diod pemancar cahaya organik (OLED). Dengan mengubah struktur molekul, sifat fizikal dan kimia, terbitan kalkon boleh disesuaikan dengan aplikasi yang diperlukan. Dalam tahun-tahun kebelakangan ini, ahli kimia telah menghasilkan banyak jenis molekul terkonjugasi-π untuk memperoleh ciri kependarkilauan yang sangat baik daripada sebatian organik, dan struktur sedemikian biasanya membawa kepada warna yang terang dan foto pendarcahaya yang sangat baik. Dalam kajian ini, terbitan kalkon tergantian yang menampilkan terephthalaldehid (N1A) sebagai penghubung-π dengan antrasena sebagai penggantian kumpulan penderma, telah disintesis melalui tindak balas pemeluwapan Claisen-Schmidt. Sebatian yang disintesis telah dicirikan menggunakan spektroskopi Lembayung Inframerah (FTIR) dan analisa Ultra Lembayung sinar nampak. Pengiraan teori fungsi ketumpatan (DFT) dilaksanakan untuk menilai kesan antrasena sebagai penggantian pendermaan elektron ke atas sifat NLO bagi terbitan kalkon tersubstitusi. Dapatan NLO bagi terbitan dualgantian ini menunjukkan kerangka molekul kalkon mempunyai ciri penting untuk aplikasi seterusnya sebagai bahan pemancar OLED.

Kata kunci: kalkon, teori fungsi ketumpatan, optik bukan linear, spektroskopi

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