Electropolymerization of cobalto(5,10,15-tris(4-aminophenyl)- 20-phenylporphyrin) for electrochemical detection of antioxidant-antipyrine
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1 Supplementary material Electropolymerization of cobalto(5,10,15-tris(4-aminophenyl)- 20-phenylporphyrin) for electrochemical detection of antioxidant-antipyrine Sambandam Anandan* a, Arumugam Manivel a, Abdullah M. Asiri b and Jerry J. Wu* c a anomaterials and Solar Energy Conversion Lab, Department of Chemistry, ational Institute of Technology, Trichy , India b The Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21413, P.O. Box 80203, Saudi Arabia c Department of Environmental Engineering and Science, Feng Chia University, Taichung 407, Taiwan Contents Synthesis pathway of cobalto(5,10,15-tris(4-aminophenyl)-20-phenylporphyrin) monomer and polymer Figures
2 Synthesis pathway of cobalto(5,10,15-tris(4-aminophenyl)-20-phenylporphyrin) monomer and polymer Synthesis of 5,10,15, 20-tetraphenylporphyrin (TPP). Pyrrole (6ml, 0.1mol) and benzaldehyde (8.8 ml, 0.1 mol) were dissolved in 200ml of propionic acid and the mixture was refluxed for about 2 hours (Scheme-1). The colour of the reaction mixture is first turned into pale red in colour and changed to black during the course of the reaction. The mixture was allowed to cool and then kept it overnight. Purple coloured crystals were separated along the wall of the reaction vessel and were filtered. The filtrate was distilled in rotovac under reduced pressure to yield a violet colour residue. The residue was thoroughly washed with hot water to remove the residual propionic acid. The solid was extracted with chloroform (CHCl 3 ) and the extract was purified using neutral alumina column for column chromatography with CHCl 3 as eluent. Bright pink coloured tetra phenyl porphyrin (TPP) was collected from the column and on removal of the solvent; a glittering violet-coloured powder of the material was obtained. The crystals were washed with hot water first to remove the propionic acid and then with methanol repeatedly to remove the impurities present in the violet coloured crystals. The purity of the material was checked up using TLC and by other characterisation techniques. Synthesis of 5,10,15-tris(4-nitrophenyl)-20-phenylporphyrin (TPP). 100 mg of 5,10,15,20-tetraphenylporphyrin in 10ml of trifluoroacetic acid (TFA) was taken in 100 ml conical flask with magnetic stirrer were kept in ice bath for 2 min (Scheme-1). After 2 min, 600 mg of sodium nitrite was added to the mixture and stirred for 3 hours at 5 C. Then, the reaction mixture was poured into 200ml of double distilled water and extracted with dichloromethane. The organic layer was washed thoroughly with saturated sodium bicarbonate and then dried using anhydrous sodium sulphate. The organic layer was distilled off and the product was purified using neutral alumina column packed with hexane for column chromatography and CHCl 3 as eluent. The material and its derivatives were characterised using 1 H MR studies. Synthesis of 5,10,15-tris(4-aminophenyl)-20-phenylporphyrin (TAPP). 100 mg of 5,10,15-Tris(4-nitrophenyl)- 20-phenylporphyrin (TPP) and 1.0 g of SnCl 2 was ground well with 1 ml of hydrochloric acid. Then the mixture was dissolved in 10 ml Conc. HCl and the mixture was heated at 90 C for 3 hours with stirring (Scheme-1). A small quantity of the mixture was drawn from the reaction mixture and diluted with water and extracted in CHCl 3. The organic layer was washed with water thoroughly, dried and checked using TLC for the conversion of nitro to amino group. When the reaction was complete, the reaction mixture was diluted with distilled water and extracted using CHCl 3. Two layers were separated out. The organic layer was washed with water till it becomes pink in colour, which is indicating the formation of the TAPP porphyrin. The organic layer was dried with anhydrous sodium sulphate, concentrated and then purified using column chromatography. The pure compound was crystallized in methanol and used for other synthetic preparations. The material and its derivatives were characterized using 1 H MR studies. Synthesis of Cobalto(5,10,15-tris(4-aminophenyl)-20-phenylporphyrin) (Co-TAPP). 25mg of free base porphyrin was dissolved in chloroform and then 50mg of Cobalt acetate was added slowly in methanol with a drop of acetic acid (Scheme-3.6). The mixture was refluxed for 60 min, occasionally checking the TLC. Insertion of Cobalt (II) was completed, when no spot of the free base porphyrin can be detected. The product formation was also indicated from the conversion of brownish pink to red colour for Co derivatives. Then the reaction mixture was cooled and washed with water repeatedly to remove the excess of inorganic metal salt, acetic acid and methanol from the reaction mixture. After washing, chloroform solution was dried over sodium sulphate and evaporated to dryness. The product was further purified using neutral alumina column packed with hexane for column chromatography and CHCl 3 as eluent. The 2
3 metalloporphyrin thus prepared were characterised using Electronic absorption spectrum in the visible region and IR spectroscopy. Scheme illustrates the synthesis pathway of Cobalto(5,10,15-Tris(4-aminophenyl)-20-phenylporphyrin) monomer and polymer O 2 H O Propionic acid Reflux, 2 Hours H H Excess ao 2 Trifluoroacetic acid H H TPP O 2 TPP O 2 H 2 H 2 SnCl 2 HCl H 2 H H TAPP H 2 (CH 3 COO) 2 Co CH 3 Cl, CH 3 OH CH 3 COOH Δ H 2 Co Co(TAPP) H 2 H GCE 0.1 M TBAClO 4 in DMF Co H poly Co(TAPP) H n 3
4 H H Fig. S1. MR spectrum of tetra phenyl porphyrin in CDCl 3 A perusal of Fig. S1 shows that four different resonance peaks were observed for TPP at 8.9 ppm, 8.25 ppm, 7.8 ppm and -2.7 ppm. TPP consists of four set of protons, which are β-pyrrole protons, ortho and meta-phenyl protons, paraphenyl protons and the imino-protons. The β-pyrrole protons are symmetric and equivalent; it cannot have any other protons to couple with. The porphyrin ring system exhibits aromatic character with 22π electrons. A diamagnetic ring current de-shields the β protons outside the macro cycle, from the external magnetic field. Hence the resonance at 8.9ppm can be attributed to the β-pyrrole protons. The signal at 8.25ppm arises due to the ortho phenyl proton, meta and para phenyl protons appear together as multiplets at 7.8 ppm. This separation arises due to the porphyrin π electrons ring current that affects dominantly the ortho protons, when compared to meta and para protons of the phenyl group. The diamagnetic ring current that deshields the protons on the outside of the macro cycle shields the H protons at middle of the ring from the external magnetic field. Thus the imino-protons shifted up field even further than the Tetramethylsilane to -2.7 ppm and appear as singlet. The integration of peak intensity is in the ratio of 4:4:6:1 and is consistent with the assignment of peaks. 4
5 O 2 H H O 2 O 2 Fig. S2. MR spectrum of TPP in CDCl 3 The MR spectrum of TPP is presented in Fig. S.2. The imino protons of the TPP appear at ppm. The ortho hydrogen of the unsubstituted phenyl ring appear around 8.2 ppm whereas, the meta and para protons appears as multiplet around 7.8 ppm. The nitro substituted phenyl ring is having six set of meta and ortho protons. The meta protons of the nitro substituted phenyl ring appears as doublet around 8.4 ppm and the ortho protons at 8.7 ppm. All the β-pyrrole protons are not symmetric. It is having three set of similar protons. In addition to β-pyrrole ring, nearby one unsubstituted phenyl group will have different environment. All these protons appear as complex pattern in the range of 8.7 ppm to 8.9 ppm. 5
6 H 2 H H H 2 H 2 Fig. S3. MR spectrum of TAPP in CDCl 3 The MR spectrum of TAPP is presented in Fig. S3. The imino protons of the TAPP are appeared at ppm. The amino protons were appeared around 4.06 ppm as singlets. The β-pyrrole protons were appeared around 8.81 ppm and 8.91ppm. The meta protons of the amino substituted phenyl ring appeared around 7.99 ppm. The ortho protons of the amino substituted phenyl ring appeared around 7.08 ppm. The meta and para position of the free phenyl ring protons were are obtained around 7.75 and ortho protons were obtained around 8.23 ppm. 6
7 Absorbance Wavelength (nm) Fig. S4. The UV visible absorbance spectrum of the TPP; the inset shows the expanded view of the Q bands 7
8 Absorbance Wavelength (nm) Fig. S5. The UV visible absorbance spectrum of the TPP; the inset shows the expanded view of the Q bands 8
9 1.5x x10-5 Current (A) 5.0x x Potential (mv) Fig. S6. The cyclic voltammogram of TPP at 100 mv/s 9
10 2.5x x x10-5 Current (A) 1.0x x x x Potential (V) Fig. S7. The cyclic voltammogram of TPP at 100 mv/s 10
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