Sains Malaysiana 53(8)(2024): 1925-1935

http://doi.org/10.17576/jsm-2024-5308-16

Synthesis, Characterisation, and Preliminary Evaluation of Bis-Indolylmethane Derivatives as Colorimetric Sensor for Metal Ions Detection

(Sintesis, Pencirian dan Penilaian Awal Terbian Bis-Indolilmetana sebagai Penderia Kolorimetrik untuk Pengesanan Ion Logam)

TENGKU SARAH TENGKU MD FAUZI¹, ZUNNUR ALWANI AHMAD ZAKI¹, WAN NUR AFIQAH WAN ANUAR¹, SYAZA AZHARI¹, NURUL HIDAYAH ABDUL RAZAK³ & NADRAHTUL HUDA MISRAL^2,*

¹Industrial Chemical Technology, Faculty of Science and Technology, Universiti Sains Islam Malaysia, Bandar Baru Nilai, 71800 Nilai, Negeri Sembilan, Malaysia

²Pusat Tamhidi, Universiti Sains Islam Malaysia, Bandar Baru Nilai, 71800 Nilai, Negeri Sembilan, Malaysia

³Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 Johor Bahru, Johor, Malaysia

Received: 5 June 2024/Accepted: 4 July 2024

Abstract

Heavy metal ions such as copper, chromium, and manganese are very harmful to both the environment and living organisms. Their presence in excess amount can harm the liver, kidneys, lungs, and other vital organs. A colorimetric sensor based on bis-indolylmethane (BIM) derivatives was preliminary studied to investigate their ability as a heavy metal ionophore with existence of H-bonding interactions between the indolic N–H functional groups and the metal ions. Five different BIM derivatives were synthesised involving condensation reaction between 2-methylindole and different substituted benzaldehydes, and were characterised using ¹H and ¹³C NMR, FT-IR, and UV-Vis spectroscopy to confirm their molecular structure. Colorimetric sensing analysis involving metal screening with Cu²⁺, Mn²⁺ and Cr⁶⁺ ions via naked eye study showed compounds 1 and 5 had the most intense colour change, hence having the highest possibility to make interaction or to be bound to the metal ions. A further binding interaction study was conducted using UV-Vis titration analysis between compound 1 with the metal ions involving Cu²⁺ and Mn²⁺ and compound 5 with Cr⁶⁺, respectively, proved the synthesized BIM derivatives to act as a potential heavy metal ions colorimetric sensor.

Keywords: Bis-indolylmethane; colorimetric sensor; metal ion

Abstrak

Ion logam berat seperti kuprum, kromium dan mangan sangat berbahaya kepada alam sekitar dan organisma hidup. Kehadiran mereka dalam jumlah yang berlebihan boleh membahayakan hati, buah pinggang, paru-paru dan organ penting lain. Penderia metri warna berdasarkan terbitan bis-indolilmetana (BIM) telah dikaji awal untuk mengkaji keupayaannya sebagai ionofor logam berat dengan kewujudan interaksi ikatan-H antara kumpulan berfungsi N-H indolik dan ion logam. Lima terbitan BIM berbeza telah disintesis melibatkan tindak balas kondensasi antara 2-metilindola dan penggantian benzaldehid berbeza dan dicirikan menggunakan spektroskopi ¹H dan ¹³C NMR, FT-IR dan UV-Vis untuk mengesahkan struktur molekulnya. Analisis penderiaan metri warna yang melibatkan penyaringan logam dengan ion Cu²⁺, Mn²⁺ dan Cr⁶⁺ melalui kajian mata kasar menunjukkan sebatian 1 dan 5 mempunyai perubahan warna yang paling ketara, justeru, mempunyai kemungkinan paling tinggi untuk melakukan interaksi atau terikat kepada ion logam. Kajian interaksi pengikatan selanjutnya telah dijalankan menggunakan analisis titratan UV-Vis antara sebatian 1 dengan ion logam yang melibatkan Cu²⁺ dan Mn²⁺ dan sebatian 5 dengan Cr⁶⁺ masing-masing membuktikan terbitan BIM yang disintesis berpotensi untuk bertindak sebagai penderia metri warna ion logam berat.

Kata kunci: Bis-indolilmetana; ion logam; penderia metri warna

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*Corresponding author; email: nadrahtulhuda@usim.edu.my