SINTESIS TURUNAN HIDRAZON DARI VANILIN SEBAGAI SENSOR KOLORIMETRI ANION
SUHARMAN, Dr. Bambang Purwono, M.Sc.
2014 | Tesis | S2 Ilmu KimiaTelah disintesis turunan hidrazon dan azo-hidrazon sebagai senyawa sensor anion. Senyawa azo 4-hidroksi-3-metoksi-5-(fenildiazenil)benzaldehida disintesis melalui reaksi diazotasi dari vanilin (reseptor 1). Senyawa 2-metoksi-6- (fenildiazenil)-4-(2-(2,4-dinitrofenil)hidrazon)metil)fenol (reseptor 3) dan 2- metoksi-6-(fenildiazenil)-4-(2-fenilhidrazon)metil)fenol ( reseptor 4) disintesis melalui reaksi edisi-eliminasi dari 4-hidroksi-3-metoksi-5-(fenildiazenil) benzaldehida dalam etanol, sedangkan senyawa 4-((2-(2,4-dinitrofenil)hidrazon) metil)-2-metoksifenol (reseptor 2) disintesis melalui reaksi adisi eliminasi dari vanilin. Sintesis senyawa azo 4-hidroksi-3-metoksi-5-(fenildiazenil)benzaldehida, reseptor 2, 3 dan 4 dihasilkan rendemen masing-masing sebesar 72; 79; 55 dan 81% . Uji reseptor 2, 3 dan 4 sebagai sensor anion dilakukan dengan menambahkan anion F-, Cl-, Br-, I-, CN-, SO4 2-, CO3 2- , CH3COO- dan H2PO4 2- . Hasil uji solvatochromic reseptor 2, 3 dan 4 menunjukan perbedaan nilai λmaks reseptor: reseptor 2 menunjukan λmaks pada (DMSO = 400 nm, asetonitril = 395 nm, aseton = 397 nm), reseptor 3 menunjukan λmaks pada (DMSO = 409 nm, asetonitril = 390 nm), reseptor 4 menunjukan λmaks pada (DMSO = 355 nm, asetonitril = 347 nm, aseton = 348 nm, etanol = 351 nm). Hasil uji sebagai sensor anion menunjukan bahwa reseptor 2, 3 dan 4 selektif terhadap anion sianida dalam pelarut asetonitril dengan nilai λmaks 472, 555 dan 510. Reseptor 3 lebih selektif sebagai sensor anion sianida dengan limit deteksi 1 mM dibandingkan dengan reseptor 2 (7 mM) dan reseptor 4 (4 mM). Kata kunci : vanilin, sensor anion, hidrazon, azo-hidrazon, adisi-eliminasi, limit deteksi
Anion sensor based on hydrazone and azo-hydrazone derivatives from vanillin have been synthesized. The azo compound of 4-hydroxy-3-methoxy-5- (phenylazo)benzaldehyde was produced by diazotation reaction of vanillin (receptor 1). The azo-hydrazone compound 2-methoxy-6-(phenyldiazenyl)-4-(2- (2,4-dinitrophenyl)hydrazone)methyl)phenol (receptor 3) and 2-methoxy-6- (phenyldiazenyl)-4-(2-phenyhydrazone)methyl)phenol ( receptor 4) were synthesized by addition-elimination reaction of 4-hydroxy-3-methoxy-5-(phenylazo) benzaldehyde, while 4-((2-(2,4-dinitrophenyl)hydrazone)methyl)-2-methoxyphenol (receptor 2) was synthesized by addition-elimination reaction of vanillin and 2,4-dinitrophenylhydrazine. Synthesis of azo 4-hydroxy-3-methoxy-5-(phenylazo)benzaldehyde, receptor 2, 3 and 4 resulted in yield 72; 79; 73 and 81% respectively. The test of receptors 2, 3 and 4 as anion sensor were carried out by addition F-, Cl-, Br-, I-, CN- , SO4 2-, CO3 2- , CH3COO- and H2PO4 2- anions. The test results as solvatochromic receptor 2, 3 and 4 showed the differences of λmax value: receptor 2 showed λmax at (DMSO = 400nm; CH3CN = 395 nm, ethanol = 397 nm); receptor 3 showed λmax at (DMSO = 355 nm; CH3CN = 390 nm); receptor 4 showed λmax at (DMSO = 355 nm; CH3CN = 347 nm; acetone = 348 nm; ethanol ; 351nm). The test results as anion sensors showed that receptor 2, 3 and 4 selective to cyanide anion in CH3CN solvent with λmax value 472, 555 and 510. Receptor 3 is more selective as cyanide anion sensor with a limit of detection 1 mM than receptor 2 (7 mM) and receptor 4 (4 mM). Keywords: vanillin, anion sensors, hydrazone, azo-hydrazone, additionelimination, limit of detection
Kata Kunci : vanilin, sensor anion, hidrazon, azo-hidrazon, adisi-eliminasi, limit deteksi; vanillin, anion sensors, hydrazone, azo-hydrazone, additionelimination, limit of detection
