Malaysian Journal of Analytical Sciences Vol 23 No 5 (2019): 763 - 770

SYNTHESIS AND CHARACTERISATION OF

4-PROPOXYBENZALDEHYDE SUBSTITUTED HECK-SCHIFF BASE COMPOUND AS SPACER IN ELECTROCHEMICAL DNA SENSOR

(Sintesis dan Pencirian Sebatian 4-Propoksibenzaldehid Gantian Heck-Schiff Bes sebagai Peruang dalam Sensor DNA Elektrokimia)

Norhafiefa Hassan¹ and Hanis Mohd Yusoff^1,2*

¹Faculty of Science and Marine Environment

²Advance Nano Materials (ANoMA) Research Group

Faculty of Science and Marine Environment,

Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia

*Corresponding author: hanismy@umt.edu.my

Received: 27 May 2019; Accepted: 25 August 2019

Abstract

Schiff base compound produced from aromatic aldehydes and aromatic amines has been used in a wide range of applications in various fields, including pharmaceutical, life sciences and chemical science (e.g. inorganic and analytical chemistry). It has also been applied in optical and electrochemical sensors to enable the detection of enhanced selectivity and sensitivity of the sensors. These compounds give excellent prospects in sensor study. In this study, Schiff base compound derived from 4-(4-nitrostyryl) aniline and 4-(4-aminostyryl)benzonitrile with 4-propoxybenzaldehyde was synthesised using ethanol as the solvent. All compounds were characterised by using the Fourier transform infrared spectroscopy (FTIR), UV-Vis spectrophotometer and Nuclear Magnetic Resonance (NMR). FTIR showed the formation of C=N (imine) stretching vibrations within the range of 1604.36 – 1606.51 cm^-1. In UV-vis, π-π* electronic transition of the C=N in both compounds was observed within the peak range of 361-385 nm. Meanwhile in the ¹H NMR, the peak of CH=N (Imine) group was found at δ 8.32-8.34 ppm, whereas for ¹³C NMR, the peaks were discovered at δ 158.72, δ 158.80 and 158.72 ppm. The application of the Schiff base as a linker in electrochemical DNA sensor (E-DNA) still has not been studied previously. In this study, two new Schiff base derivatives were synthesised and characterised due to its promising potential in sensors, which prompted its application as a future potential linker in electrochemical DNA sensor.

Keywords: Schiff base, synthesis, spacer, E-DNA sensor

Abstrak

Sebatian Schiff bes yang dihasilkan daripada aromatik aldehid dan aromatik amina telah digunakan dalam pelbagai aplikasi dalam pelbagai bidang termasuk farmaseutikal, sains hayat dan sains kimia termasuk kimia tak organik dan analisis kimia. Ia juga telah digunakan dalam sensor optik dan elektrokimia untuk membolehkan pengesanan meningkatkan pemilihan dan kepekaan sensor. Sebatian ini mungkin memberi prospek yang sangat baik dalam sensor. Sebatian Schiff bes yang diterbitkan daripada 4-(4-nitrostiril) anilina dan 4-(4-aminostiril) benzonitril dengan 4-propoksibenzaldehid disintesis menggunakan etanol sebagai pelarut. Kesemua sebatian telah dicirikan oleh spektroskopi inframerah transformasi Fourier (FTIR), UV-Vis spektrofotometer dan Resonans Magnet Nukleus (NMR). FTIR menunjukkan pembentukan C=N (imina) perengangan getaran pada julat 1604.36 – 1606.51 cm^-1. Dalam UV-Vis, peralihan elektron π-π* imina untuk kedua-dua sebatian diperhatikan pada julat puncak 361-385 nm. Sementara itu, puncak ¹H NMR untuk kumpulan CH=N (imina) telah dijumpai pada δ 8.32-8.34 ppm dan untuk ¹³C NMR puncaknya telah dijumpai pada δ 158.80 dan 158.72 ppm. Aplikasi terbitan Schiff bes sebagai penyambung dalam sensor DNA elekrokimia (E-DNA) masih belum dikaji. Dalam kajian ini, dua terbitan Schiff bes yang baru telah disintesis dan dicirikan kerana ia menjanjikan sensor yang mendorong kita untuk menggunakannya sebagai penyambung potensi masa depan dalam sensor DNA elektrokimia.

Kata kunci: Schiff bes, sintesis, pencirian, peruang, sensor E-DNA

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