Synthesis and Spectral Evaluation of Some Unsymmetrical Mesoporphyrinic Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Infrared Spectra
2.2. Absorption Spectra
2.3. Fluorescence Emissions, Lifetimes and Singlet Oxygen Formation
3. Experimental Section
3.1. Materials and Methods
3.2. Synthesis of Zn(II)-5-(4-Acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)porphyrin (Zn(II)TCMPOMO) and Zn(II)-5-[(3,4-Methylenedioxy)phenyl]-10,15,20-tris-(4-carboxymethylphenyl) porphyrin (Zn(II)TRMOPP)
3.3. Synthesis of Cu(II)-5-(4-Acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)porphyrin (Cu(II)TCMPOMO) and Cu(II)-5-[(3,4-Methylenedioxy)phenyl]-10,15,20-tris-(4-carboxymethylphenyl) porphyrin (Cu(II)TRMOPP)
4. Conclusions
Acknowledgements
References
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Assignments | Zn(II)TCMPOMO | Cu(II)TCMPOMO | Zn(II)TRMOPP | Cu(II)TRMOPP |
---|---|---|---|---|
νC–H | 2920m | 2921m | 2922w | 2924w |
νC–H from –O–CH2–O– | - | - | 2915m | 2916m |
νC–H from –O–CH3 | 2850m | 2851m | 2850m | 2850m |
νC = O | 1723m | 1724m | 1722m | 1725m |
νC–N | 1606m | 1602m | 1605m | 1606m |
νC = N | 1510m | 1500m | 1492m | 1496m |
νC–H pyrrole | 1456w | 1458w | 1433w | 1433w |
νC–O | 1190s | 1188m | 1198s | 1195s |
δC–H | 997m | 1000m | 996m | 999m |
γC–C | 867w | 865w | 867w | 867w |
γC–N pyrrole | 795m | 799m | 780m | 792m |
Solvent | λmax (nm) [lg ɛ (L·mol−1·cm−1)] | ||
---|---|---|---|
Soret band B(0,0) | Q bands Qy(0,0) | Qx(1,0) | |
Zn(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)porphyrin | |||
EtOH | 426.2 [5.646] | 558.6 [4.203] | 599.3 [3.783] |
iso-PrOH | 427.0 [5.641] | 558.6 [4.271] | 599.1 [3.932] |
CHCl3 | 422.6 [5.584] | 549.8 [4.261] | 589.5 [3.690] |
DMF | 428.9 [5.602] | 560.3 [4.201] | 601.4 [3.914] |
DMSO | 431.5 [5.588] | 562.0 [4.227] | 602.7 [3.979] |
Cu(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)porphyrin | |||
EtOH | 413.0 [5.629] | 537.0 [4.095] | - |
iso-PrOH | 414.1 [5.507] | 537.1 [4.174] | - |
CHCl3 | 416.3 [5.539] | 539.9 [4.325] | - |
DMF | 417.0 [5.565] | 540.1 [4.142] | - |
DMSO | 420.8 [5.479] | 544.0 [4.261] | - |
Zn(II)-5-[(3,4-methylenedioxy)phenyl]-10,15,20-tris-(4-carboxymethylphenyl)porphyrin | |||
EtOH | 426.0 [5.687] | 558.2 [4.292] | 598.7 [3.924] |
iso-PrOH | 426.3 [5.671] | 558.4 [4.274] | 598.7 [3.903] |
CHCl3 | 422.0 [5.572] | 549.3 [4.271] | 587.2 [3.680] |
DMF | 429.0 [5.635] | 559.8 [4.255] | 601.0 [3.944] |
DMSO 1 | 431.0 [5.632] | 561.9 [4.246] | 603.0 [3.964] |
Cu(II)-5-[(3,4-methylenedioxy)phenyl]-10,15,20-tris-(4-carboxymethylphenyl)porphyrin | |||
EtOH | 414.1 [5.778] | 538.0 [4.447] | - |
iso-PrOH | 414.1 [5.772] | 538.0 [4.435] | - |
CHCl3 | 416.2 [5.698] | 539.4 [4.387] | - |
DMF | 418.2 [5.668] | 540.8 [4.394] | - |
DMSO 1 | 422.3 [5.652] | 544.4 [4.408] | - |
Porphyrinic compounds | ΦΔ | ΦF | τF (ns) |
---|---|---|---|
TCMPOMO | 0.42 | 0.09 | 7.89 |
Cu(II)TCMPOMO | 0.08 | <0.01 | 1.90 |
Zn(II)TCMPOMO | 0.16 | 0.06 | 1.75 |
Cu(II)TRMOPP | 0.04 | <lod * | <lod * |
Zn(II)TRMOPP | 0.24 | 0.06 | 1.71 |
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Boscencu, R.; Oliveira, A.S.; Ferreira, D.P.; Ferreira, L.F.V. Synthesis and Spectral Evaluation of Some Unsymmetrical Mesoporphyrinic Complexes. Int. J. Mol. Sci. 2012, 13, 8112-8125. https://doi.org/10.3390/ijms13078112
Boscencu R, Oliveira AS, Ferreira DP, Ferreira LFV. Synthesis and Spectral Evaluation of Some Unsymmetrical Mesoporphyrinic Complexes. International Journal of Molecular Sciences. 2012; 13(7):8112-8125. https://doi.org/10.3390/ijms13078112
Chicago/Turabian StyleBoscencu, Rica, Anabela Sousa Oliveira, Diana P. Ferreira, and Luís Filipe Vieira Ferreira. 2012. "Synthesis and Spectral Evaluation of Some Unsymmetrical Mesoporphyrinic Complexes" International Journal of Molecular Sciences 13, no. 7: 8112-8125. https://doi.org/10.3390/ijms13078112