Fluorescence and FTIR Spectra Analysis of Trans-A2B2-Substituted Di- and Tetra-Phenyl Porphyrins
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation of Asymmetric Di- and Tetra-phenyl Porphyrin Compounds
4 | 5 | 6 | |
---|---|---|---|
Formula | C68H76N4O4Zn1 | C22H22N2OZn0.50.5 | C58H52Cl6N6O6Zn |
f.w. (g.mol-1) | 1078.77 | 363.12 | 1207.18 |
Cryst. Syst. | Orthorhombic | Triclinic | Triclinic |
Space group | Pbcn (No. 60) | P-1 (No. 2) | P-1 (No. 2) |
a (Å) | 18.923 (5) | 9.721 (5) | 10.877 (5) |
b (Å) | 11.138 (5) | 10.593 (5) | 13.726 (5) |
c (Å) | 28.542 (5) | 10.679 (5) | 18.728 (5) |
α (o) | 90 | 64.838 (5) | 88.050 (5) |
β (o) | 90 | 67.222 (5) | 87.781 (5) |
γ (o) | 90 | 89.723 (5) | 84.908 (5) |
V (Å3) | 6016 (3) | 900.7 (8) | 2782 (2) |
Z | 4 | 2 | 2 |
T (K) | 300 | 293 | 120 |
Dx (g.cm-3) | 1.191 | 1.339 | 1.441 |
μ (mm-1) | 0.46 | 0.73 | 3.73 |
R(F) a, I>2σ(Fo) | 0.064 | 0.117 | 0.139 |
Rw(F2) b, I>2σ(Fo) | 0.201 | 0.247 | 0.143 |
S | 0.95 | 1.03 | 1.05 |
Rint | 0.033 | 0.044 | 0.066 |
θmax | 29.2° | 29.4 | 62.8° |
Δρmin | -0.84 e Å-1 | -1.32 e Å-1 | -0.19 e Å-1 |
Δρmax | 0.85 e Å-1 | 4.70 e Å-1 | 0.19 e Å-1 |
2.2. FTIR Spectra and Analysis of Vibration Structure
2.1.1. General appearance of FTIR spectra
2.2.2. Vibrations of phenyl and pyrrole rings
2.2.3. Deformation vibrations
2.2.4. The influence of the nitro-group
2.2.5. Specific porphyrin ring modes in comparison with other studies
2.3. Optical Absorption, Excited States and Fluorescence
2.3.1. Theoretical and experimental absorption spectra
Sample | Absorbance (nm) | Emission wavelength (nm) [decay time (ns)] | Quantum Efficiency a |
---|---|---|---|
1 | S: 421; Q: 517; 554; 596; 652 | 656 [4.5]; 721 [4.5] | 0.13 |
4 | S: 427; Q: 558; 595 | 607 [1.3]; 657 [1.3 and 8.7] | 0.05 |
2 | S: 409; Q: 503; 538; 578; 634 | 637 [5.2]; 700 [5.2] | 0.06 |
5 | S: 414; Q: 545; 580(w) | 587 [2.4]; 638 [2.4] | 0.03 |
3 | S: 423; Q: 517; 554; 593; 650 | 655 [5.0]; 720 [5.1] | 0.13 |
6 | S: 428; Q: 559; 602 | 622 [1.40] | 0.07 |
Compound | № | λ | E | F | Assignment |
---|---|---|---|---|---|
2 | 1 | 569.9 | 2.18 | 0.0206 | HOMO→LUMO+1(+45%) HOMO-1→LUMO(+30%) |
2 | 535.5 | 2.32 | 0.0525 | HOMO→L+0(+44%) HOMO-1→LUMO+1(27%) | |
3 | 391.6 | 3.17 | 1.1557 | HOMO-1→LUMO+1(+24%) HOMO-3→LUMO(18%) | |
4 | 384.0 | 3.23 | 0.5538 | HOMO-1→LUMO(+21%) HOMO-3→LUMO(+12%) | |
5 | 381.3 | 3.25 | 0.0513 | HOMO-2→LUMO(+85%) | |
5 | 1 | 529.5 | 2.34 | 0.0001 | HOMO→LUMO(+56%) HOMO-1→LUMO+1(47%) |
2 | 528.4 | 2.35 | 0.0164 | HOMO→LUMO+1(+57%) HOMO-1→LUMO(+45%) | |
3 | 386.5 | 3.21 | 1.2378 | HOMO-3→LUMO+1(+38%) HOMO-1→LUMO(+25%) | |
4 | 379.7 | 3.27 | 0.3924 | HOMO-3→LUMO(31%) HOMO-1→LUMO+1(+24%) | |
5 | 376.1 | 3.30 | 0.0201 | HOMO-2→LUMO+1(+92%) | |
6 | 371.9 | 3.33 | 0.0003 | HOMO-2→LUMO(+98%) | |
7 | 358.8 | 3.46 | 0.0000 | HOMO-4→LUMO(+95%) | |
8 | 357.4 | 3.47 | 0.0000 | HOMO-4→LUMO+1(+94%) | |
9 | 352.0 | 3.52 | 0.5981 | HOMO-3→LUMO+1(+57%) HOMO-1→LUMO(13%) | |
10 | 350.0 | 3.54 | 0.3016 | HOMO-3→LUMO(+61%) HOMO-1→LUMO+1(+9%) | |
3 | 1 | 590.3 | 2.10 | 0.0457 | HOMO→LUMO(+43%) HOMO→LUMO+1(+25%) |
2 | 554.4 | 2.24 | 0.0689 | HOMO→LUMO+1(+36%) HOMO→LUMO(26%) | |
3 | 492.5 | 2.52 | 0.0061 | HOMO→LUMO+2(+96%) | |
4 | 481.1 | 2.58 | 0.0961 | HOMO→LUMO+3(+83%) HOMO-1→LUMO+1(+9%) | |
5 | 441.1 | 2.81 | 0.1676 | HOMO-1→LUMO+3(+44%) HOMO-1→LUMO(+24%) | |
6 | 438.3 | 2.83 | 0.0366 | HOMO-1→LUMO+2(+80%) HOMO-1→LUMO+3(+12%) | |
7 | 409.5 | 3.03 | 0.0004 | HOMO-2→LUMO(+97%) | |
8 | 405.8 | 3.06 | 0.1798 | HOMO-3→LUMO(+72%) HOMO-1→LUMO+1(10%) | |
9 | 403.0 | 3.08 | 0.5780 | HOMO-3→LUMO+1(+44%) HOMO-1→LUMO+3(22%) | |
10 | 400.2 | 3.10 | 0.0256 | HOMO-2→LUMO+1(+92%) | |
6 | 1 | 552.3 | 2.24 | 0.0469 | HOMO→LUMO(+65%) HOMO-1→LUMO+1(36%) |
2 | 544.0 | 2.28 | 0.0100 | HOMO→LUMO+1(+54%) HOMO-1→LUMO(+46%) | |
3 | 476.7 | 2.60 | 0.0095 | HOMO→LUMO+2(+95%) | |
4 | 468.1 | 2.65 | 0.1128 | HOMO→LUMO+3(+77%) HOMO→LUMO(9%) | |
5 | 447.4 | 2.77 | 0.0164 | HOMO-1→LUMO+2(+85%) HOMO-1→LUMO+3(9%) | |
6 | 444.6 | 2.79 | 0.0870 | HOMO-1→LUMO+3(+58%) HOMO-1→LUMO(18%) | |
7 | 403.3 | 3.07 | 0.0039 | HOMO-2→LUMO(+96%) | |
1 | 1 | 581.4 | 2.13 | 0.0245 | HOMO→LUMO+1(+61%) HOMO-1→LUMO(30%) |
2 | 544.3 | 2.28 | 0.0440 | HOMO→LUMO(+59%) HOMO-1→LUMO+1(+32%) | |
3 | 399.7 | 3.10 | 0.9878 | HOMO-1→LUMO(+48%) HOMO→LUMO+1(+22%) | |
4 | 390.6 | 3.17 | 1.1135 | HOMO-1→LUMO+1(+43%) HOMO→LUMO(23%) | |
5 | 385.3 | 3.22 | 0.0247 | HOMO-2→LUMO+1(+55%) HOMO-2→LUMO(39%) | |
6 | 382.8 | 3.24 | 0.0034 | HOMO-2→LUMO(+51%) HOMO-2→LUMO+1(+34%) | |
7 | 378.8 | 3.27 | 0.0145 | HOMO-3→LUMO+1(+69%) HOMO-6→LUMO+1(8%) | |
4 | 1 | 540.7 | 2.29 | 0.0162 | HOMO→LUMO(+57%) HOMO-1→LUMO+1(+38%) |
2 | 540.5 | 2.29 | 0.0157 | HOMO→LUMO+1(+57%) HOMO-1→LUMO(39%) | |
3 | 391.9 | 3.16 | 1.1281 | HOMO-1→LUMO+1(+34%) HOMO→LUMO(23%) | |
4 | 390.7 | 3.17 | 1.1551 | HOMO-1→LUMO(+35%) HOMO→LUMO+1(+25%) | |
5 | 380.1 | 3.26 | 0.0156 | HOMO-2→LUMO(+52%) HOMO-2→LUMO+1(43%) | |
6 | 377.4 | 3.28 | 0.0002 | HOMO-2→LUMO+1(+44%) HOMO-2→LUMO(+36%) | |
7 | 372.2 | 3.33 | 0.0140 | HOMO-3→LUMO(+87%) HOMO-3→LUMO+1(+6%) |
3. Methods
3.1. Quantum Chemical Calculations
3.2. Optical and Luminescence Spectroscopy
3.3. FTIR Spectroscopy
3.4. X-Ray Diffraction
3.5. NMR Characterization
3.6. Synthesis of Compounds
3.6.1. Synthesis of 1: 5,10,15,20-tetra(4-hexyloxyphenyl) porphyrin
3.6.2. General procedure for the preparation of trans-A2B2 meso-tetraarylporphyrins
3.6.3. Synthesis of 2: 5,15-bis(4-hexyloxyphenyl) porphyrin
3.6.4. Synthesis of 3: 5,15-bis-(4-nitrophenyl)-10,20-bis(4-hexyloxyphenyl) porphyrin
3.6.5. Preparation of Zn-porphyrins: method A
3.6.6. Preparation of Zn-porphyrins: method B
3.6.7. Synthesis of 4: [5,10,15,20-tetra(4-hexyloxyphenyl) porphyrinato] zinc(II)
3.6.8. Synthesis of 5: [5,15-bis(4-hexyloxyphenyl) porphyrinato] zinc(II)
3.6.9. Synthesis of 6: [5,15-bis-(4-nitrophenyl)-10,20-bis(4-hexyloxyphenyl) porphyrinato] zinc(II)
4. Conclusions
Acknowledgements
Supporting information
References and Notes
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Şen, P.; Hirel, C.; Andraud, C.; Aronica, C.; Bretonnière, Y.; Mohammed, A.; Ågren, H.; Minaev, B.; Minaeva, V.; Baryshnikov, G.; et al. Fluorescence and FTIR Spectra Analysis of Trans-A2B2-Substituted Di- and Tetra-Phenyl Porphyrins. Materials 2010, 3, 4446-4475. https://doi.org/10.3390/ma3084446
Şen P, Hirel C, Andraud C, Aronica C, Bretonnière Y, Mohammed A, Ågren H, Minaev B, Minaeva V, Baryshnikov G, et al. Fluorescence and FTIR Spectra Analysis of Trans-A2B2-Substituted Di- and Tetra-Phenyl Porphyrins. Materials. 2010; 3(8):4446-4475. https://doi.org/10.3390/ma3084446
Chicago/Turabian StyleŞen, Pınar, Catherine Hirel, Chantal Andraud, Christophe Aronica, Yann Bretonnière, Abdelsalam Mohammed, Hans Ågren, Boris Minaev, Valentina Minaeva, Gleb Baryshnikov, and et al. 2010. "Fluorescence and FTIR Spectra Analysis of Trans-A2B2-Substituted Di- and Tetra-Phenyl Porphyrins" Materials 3, no. 8: 4446-4475. https://doi.org/10.3390/ma3084446