sintesis senyawa kemosensor warna dan fluoresen dari vanilin untuk deteksi anion

RAHMAWATI, Drs. Bambang Purwono, M.Sc., Ph.D.

2019 | Disertasi | DOKTOR KIMIA

Sintesis Senyawa Kemosensor Warna Dan Fluoresen Dari Vanilin Untuk Deteksi Anion Oleh Rahmawati NIM 14/374047/SPA/519 Intisari Senyawa kemosensor yang berasal dari vanilin telah disintesis, memanfaatkan gugus karbonil yang reaktif terhadap elektrofil. Sensor 4-(1H-benzo[d]imidazol-2-il)-2-metoksifenol (S1) dan 4-(1H-benzo[d]oksazol-2-il)-2-metoksifenol (S3) disintesis langsung dari vanilin, 4-(1H-benzo[d]imidazole-2-yl)-2-methoxy -6-nitrophenol (S2) dan 4-(1H-benzo[d]oksazol-2-il)-2-metoksi -6-nitrofenol (S4) disintesis dari 5-nitrovanilin, (E)-4-(1H-benzo[d]imidazole-2-yl)-2-methoxy-6-(phenildiazenyl)fenol (S5) dan (E)-4-(1H-benzo[d]imidazol-2-il)-2-metoksi-6-((4-nitrofenil)diazenil)fenol (S6) disintesis dari S1, (E)-4-(1H-benzo[d]oxazole-2-yl)-2-methoxy-6-(phenildiazenyl)fenol (S7) disintesis dari S3, 2-(4-hidroksi-3-metoksisikloheksil)-4H-krom-4-on (S8) disintesis dari kalkon asal vanilin. Gugus OH vanilin dipertahankan karena digunakan sebagai sisi ikat yang berinteraksi dengan anion untuk menghasilkan perubahan warna dan fluoresen. Pengujian terhadap anion-anion memperlihatkan bahwa sensor S1-S8 bersifat aktif sebagai kemosensor. S1 bersifat fluoresen selektif terhadap anion CN, S2 bersifat berwana terhadap anion CN, F, dan anion fosfat, S3 bersifat dual sensor selektif terhadap anion CN, S4 bersifat fluoresen selektif terhadap anion CN, S5 bersifat dual sensor selektif terhadap anion CN, S6 bersifat berwarna terhadap anion CN dan F, S7 bersifat dual sensor selektif terhadap anion CN, S8 bersifat dual sensor terhadap anion CN dan fluoresen terhadap anion F-. Analisis kuantitatif dalam bentuk LOD dan kass terhadap interaksi host-guest S1-S8 dengan anion menghasilkan LOD terendah sebesar 0,000012 M pada interaksi S8-CN-, nilai kass terbesar yakni 20000000/M pada interaksi S3-CN, dan model interaksinya terjadi pada model rasio 1:1, 1:2, dan 2:1. Berdasarkan hasil pengujian anion maka sensor S1-S8 ini diarahkan untuk deteksi anion CN. Kata Kunci: kemosensor, anion, vanilin

Synthesis Of Colorimetric And Fluorescence Chemosensor Compounds From Vanillin For Anion Detection By Rahmawati NIM 14/374047/SPA/519 Abstract Chemosensor compounds derived from vanillin have been synthesized, utilizing carbonyl groups that are reactive to electrophiles. Sensors 4-(1H-benzo[d]imidazole-2-il)-2-methoxyphenol (S1) and 4-(1H-benzo[d]oxazol-2-il)-2-metoxyphenol (S3) were synthesized directly from vanillin, 4-(1H-benzo[d]imidazole-2-yl)-2-methoxy -6-nitrophenol (S2) and 4-(1H-benzo[d]oxazole-2-il)-2-methoxy -6-nitrophenol (S4) was synthesized from 5-nitrovanilin, (E)-4- (1H-benzo[d]imidazole-2-yl)-2-methoxy-6-(phenildiazenyl)phenol (S5) and (E)-4-(1H-benzo[d]imidazole-2-il)-2-methoxy-6-((4-nitrophenyl)diazenil)phenol (S6) were synthesized from S1, (E)-4-(1H-benzo[d]oxazole-2-yl)-2-methoxy-6-(phenildiazenyl)phenol (S7) was synthesized from S3, 2-(4-hydroxy-3-methoxycyclohexyl)-4H-chrome-4-on (S8) was synthesized from chalcone from vanillin. The vanillin OH group was maintained because it was used as a binding side that interacts with the anion to produce color changes and fluorescence. The testing of anions showed that the S1-S8 sensors were active as sensory chemicals. S1 was selectively fluorescent to CN anions, S2 had a colored character to CN, F, and phosfat anions, S3 was dual sensor selective to CN, S4 was selectively fluorescent to CN- ion, S5 was selective sensor to CN ion, S6 was colored to CN and F, S7 was a selective dual sensor to CN, S8 was a dual sensor to CN and fluorescent to F anions. Quantitative analysis in the form of LOD and cash on the host-guest S1-S8 interaction with ananions produced the lowest LOD of 0,000012 M in the S8-CN interaction, the largest kass value was 20000000/M on S3-CN- interactanions, and the interaction model occurs in the model ratio of 1:1, 1:2, and 2:1. Based on the results of the testing of anions, the S1-S8 sensors were directed for CN anions detection. Keywords: chemosensor, vanillin, anion.

Kata Kunci : kemosensor, anion, vanilin