To the mixture, pyrrole of 0.67 g/10 mmol in propionic acid of 15 mL was fed
gradually for 30 min with controlled stirring for next 60 min at 130–140
C. The
purple solid product was then obtained. This was separated by removal of 2/3
propionic acid using rotary evaporator and finally washing with methanol followed
by diethyl ether, 3 Â 25 mL. The NH protons inside the ring of porphyrins acquired
acidic character and therefore can get deprotonated to provide porphyrin to ions
(Rabbani et al. 2016; Min et al. 2019). %Yield ¼ 71.99% and melting point ¼ above
250
C were found.
1 H NMR (400 MHz, DMSO-d 6 ): δ À1.006 (s, 2H), 0.05(t, 5H, J ¼ 7.62 Hz), 0.24
(s, 2H), 1.21(q, 3H, J ¼ 7.88 Hz), 1.54(s, 3H), 1.99(q, 2H, J ¼ 6.1 Hz), 3.74(q, 3H,
J ¼ 7.21 Hz), 4.72(brs, 5H), 6.17(s, 7H), 6.57(m, 9H), 6.69(q, 4H, J ¼ 3.17 Hz), 6.84
(q, 7H, J ¼ 3.00 Hz), 6.98(d, 4H, J ¼ 8.58 Hz), 7.07(q, 4H, J ¼ 3.19 Hz), 7.10(s,
5H), 8.49(s, 6H), 8.86(s, 2H), 12.21(s, 2H). FT-IR – (KBr, v/cm
À1 ): 3026, 2929,
1712, 1610, 1560, 1502, 1438, 1330, 1255, 1182, 991, 827, 744, 601, 464.
Synthesis of 1,1
0 1
00 -(((1
9 -(5-((3-(4-(sec-butyl)benzyl)-1H-benzo[d]imidazole-3ium-1-yl)methyl)-2-hydroxyphenyl)-1
2 ,1
3 -dihydro-1
12
H,3
2 H-1
1
λ
2
–1(12,3)-1λ
2
–
5,8-(azeno)pyrrolo[1,2-b][1]zinc[2,11]diazacycloundecina-3(5,2)pyrrolacycloheptaphan-5-ene-14,2,4-triyl)tris(4-hydroxybenzene-3,1-diyl))tris
(methylene))tris(3-(2-carboxyethyl)-1H-benzo[d]imidazole-3-ium) tribromide
chloride, polymer supported ionic liquid iron porphyrin complex 1-D
Polymer-supported ionic liquid iron porphyrin complex was successfully prepared and characterized by the different methods. The complex ligand 1-C of
0.903 g/0.5 mmol and FeCl 3 of 0.097 g/0.6 mmol were charged to methanol and
stirred initially for 30 min at atmospheric temperature. Later, above mixture was
subjected to reflux at a temperature of 75
C for 5 h in the inert atmosphere of
nitrogen. The synthesized product was then isolated by periodic washing using
methanol, and it was dried in the oven for 2 h at a temperature of 80
C. Finally, a
purple color powder of polymer-supported ionic liquid iron porphyrin complex was
obtained as given in Fig. 12.3 with yield of 79.93% and melting point of above
250
C.
Fig. 12.3 Synthesis of polymer-supported ionic liquid Fe-porphyrin complex
12 Functionalized Ionic Liquids for the Photodegradation of Dyes
401
gradually for 30 min with controlled stirring for next 60 min at 130–140
C. The
purple solid product was then obtained. This was separated by removal of 2/3
propionic acid using rotary evaporator and finally washing with methanol followed
by diethyl ether, 3 Â 25 mL. The NH protons inside the ring of porphyrins acquired
acidic character and therefore can get deprotonated to provide porphyrin to ions
(Rabbani et al. 2016; Min et al. 2019). %Yield ¼ 71.99% and melting point ¼ above
250
C were found.
1 H NMR (400 MHz, DMSO-d 6 ): δ À1.006 (s, 2H), 0.05(t, 5H, J ¼ 7.62 Hz), 0.24
(s, 2H), 1.21(q, 3H, J ¼ 7.88 Hz), 1.54(s, 3H), 1.99(q, 2H, J ¼ 6.1 Hz), 3.74(q, 3H,
J ¼ 7.21 Hz), 4.72(brs, 5H), 6.17(s, 7H), 6.57(m, 9H), 6.69(q, 4H, J ¼ 3.17 Hz), 6.84
(q, 7H, J ¼ 3.00 Hz), 6.98(d, 4H, J ¼ 8.58 Hz), 7.07(q, 4H, J ¼ 3.19 Hz), 7.10(s,
5H), 8.49(s, 6H), 8.86(s, 2H), 12.21(s, 2H). FT-IR – (KBr, v/cm
À1 ): 3026, 2929,
1712, 1610, 1560, 1502, 1438, 1330, 1255, 1182, 991, 827, 744, 601, 464.
Synthesis of 1,1
0 1
00 -(((1
9 -(5-((3-(4-(sec-butyl)benzyl)-1H-benzo[d]imidazole-3ium-1-yl)methyl)-2-hydroxyphenyl)-1
2 ,1
3 -dihydro-1
12
H,3
2 H-1
1
λ
2
–1(12,3)-1λ
2
–
5,8-(azeno)pyrrolo[1,2-b][1]zinc[2,11]diazacycloundecina-3(5,2)pyrrolacycloheptaphan-5-ene-14,2,4-triyl)tris(4-hydroxybenzene-3,1-diyl))tris
(methylene))tris(3-(2-carboxyethyl)-1H-benzo[d]imidazole-3-ium) tribromide
chloride, polymer supported ionic liquid iron porphyrin complex 1-D
Polymer-supported ionic liquid iron porphyrin complex was successfully prepared and characterized by the different methods. The complex ligand 1-C of
0.903 g/0.5 mmol and FeCl 3 of 0.097 g/0.6 mmol were charged to methanol and
stirred initially for 30 min at atmospheric temperature. Later, above mixture was
subjected to reflux at a temperature of 75
C for 5 h in the inert atmosphere of
nitrogen. The synthesized product was then isolated by periodic washing using
methanol, and it was dried in the oven for 2 h at a temperature of 80
C. Finally, a
purple color powder of polymer-supported ionic liquid iron porphyrin complex was
obtained as given in Fig. 12.3 with yield of 79.93% and melting point of above
250
C.
Fig. 12.3 Synthesis of polymer-supported ionic liquid Fe-porphyrin complex
12 Functionalized Ionic Liquids for the Photodegradation of Dyes
401