Femto- to Millisecond Time-Resolved Photodynamics of a Double-Functionalized Push–Pull Organic Linker: Potential Candidate for Optoelectronically Active MOFs
Abstract
:1. Introduction
2. Results and Discussion
2.1. Steady-state UV-Vis Absorption and Emission Studies
2.2. Time-correlated Single Photon Counting Emission Studies
2.3. Femtosecond Time-resolved Transient Absorption Studies
2.4. Flash Photolysis Transient Absorption Studies
3. Experimental part
3.1. Materials
3.2. Synthesis of Dimethyl 4-amino-8-cyanonaphthalene-2,6-dicarboxylate (Me2CANADC)
3.3. Methods
3.3.1. Materials Characterization Techniques
3.3.2. Steady-state and Time-resolved Characterization Techniques
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Solvent | Number | ∆f | η (cP) | λabs (nm) | λem (nm) | Stokes Shift (cm−1) | Φ | τ (ns) | kr b (107 s−1) | knr b (107 s−1) |
---|---|---|---|---|---|---|---|---|---|---|
DE | 1 | 0.162 | 0.23 | 425 | 512 | 3998 | 0.40 | 17.6 | 2.27 | 3.41 |
THF | 2 | 0.220 | 0.48 | 431 | 534 | 4475 | 0.28 | 14.7 | 1.90 | 4.90 |
DCM | 3 | 0.230 | 0.43 | 408 | 506 | 4747 | 0.45 | 17.3 | 2.54 | 3.24 |
ACN | 4 | 0.330 | 0.35 | 419 | 542 | 5416 | 0.16 | 14.2 | 1.06 | 5.99 |
MeOH | 5 | 0.333 | 0.58 | 430 | 559 | 5367 | 0.10 | 8.9 | 1.12 | 10.11 |
1-ProOH | 6 | 0.296 | 2.22 | 436 | 557 | 4982 | 0.14 | 11.2 a | 1.25 | 7.68 |
1-ButOH | 7 | 0.286 | 2.90 | 436 | 557 | 4982 | 0.15 | 11.5 a | 1.30 | 7.39 |
1-OctOH | 8 | 0.241 | 8.46 | 436 | 553 | 4853 | 0.20 | 13.1 a | 1.53 | 6.11 |
1-DecOH | 9 | 0.217 | 13.19 | 437 | 551 | 4734 | 0.25 | 13.8 a | 1.81 | 5.43 |
Solvent | λobs/nm | τ1/ps | A1 (%) | C1 (%) | τ2/ps | A2 (%) | C2 (%) | τ3/ns | A3 (%) | C3 (%) |
---|---|---|---|---|---|---|---|---|---|---|
1-ProOH | 500 | 66 | 75 | 2 | - | - | - | 11.2 | 25 | 98 |
525 | 66 | 49 | 1 | - | - | - | 11.2 | 51 | 99 | |
550 | 66 | 28 | <1 | - | - | - | 11.2 | 72 | >99 | |
575 | 66 | 13 | <1 | - | - | - | 11.2 | 87 | >99 | |
600 | - | - | - | - | - | - | 11.2 | 100 | 100 | |
650 | - | - | - | - | - | - | 11.2 | 100 | 100 | |
1-ButOH | 500 | 85 | 71 | 2 | - | - | - | 11.5 | 29 | 98 |
525 | 85 | 52 | 1 | - | - | - | 11.5 | 48 | 99 | |
550 | 85 | 27 | <1 | - | - | - | 11.5 | 73 | >99 | |
575 | - | - | - | - | - | - | 11.5 | 100 | 100 | |
600 | - | - | - | - | - | - | 11.5 | 100 | 100 | |
650 | - | - | - | - | - | - | 11.5 | 100 | 100 | |
1-OctOH | 500 | 160 | 61 | 3 | 550 | 14 | 2 | 13.1 | 25 | 95 |
525 | 160 | 33 | 1 | 550 | 17 | 1 | 13.1 | 50 | 98 | |
550 | 160 | −100 | −100 | 550 | 14 | 1 | 13.1 | 86 | 99 | |
575 | 160 | −100 | −100 | - | - | - | 13.1 | 100 | 100 | |
600 | 160 | −100 | −100 | - | - | - | 13.1 | 100 | 100 | |
650 | 160 | −100 | −100 | - | - | - | 13.1 | 100 | 100 | |
1-DecOH | 500 | 280 | 60 | 4 | 955 | 12 | 3 | 13.8 | 28 | 93 |
525 | 280 | 31 | 1 | 955 | 15 | 2 | 13.8 | 54 | 97 | |
550 | 280 | −100 | −100 | 955 | 9 | 1 | 13.8 | 91 | 99 | |
575 | 280 | −100 | −100 | - | - | - | 13.8 | 100 | 100 | |
600 | 280 | −100 | −100 | - | - | - | 13.8 | 100 | 100 | |
650 | 280 | −100 | −100 | - | - | - | 13.8 | 100 | 100 |
Solvent | τ1 (fs) | A1 (%) | τ2 (ps) | A2 (%) | τ3 (ps) | A3 (%) |
---|---|---|---|---|---|---|
DE | 50 | −100 | 0.33 | 100 | - | - |
THF | 100 | −93 | 2.06 | 100 | 23 | −7 |
DCM | 195 | −00 | 0.37 | 68 | 4.1 | 32 |
ACN | 95 | −100 | 0.22 | 36 | 1.8 | 64 |
MeOH | 70 | −100 | 0.54 | 30 | 9.5 | 70 |
Solvent | N2 | Air | O2 | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
τ1 (ns) | A1 (%) | τ2 (µs) | A2 (%) | τ1 (ns) | A1 (%) | τ2 (µs) | A2 (%) | τ1 (ns) | A1 (%) | τ2 (µs) | A2 (%) | |
DE | - | - | 1.8 | 100 | 444 | 15 | 2.0 | 85 | 64 | 33 | 1.9 | 67 |
THF | 501 | 11 | 2.0 | 89 | 236 | 18 | 2.0 | 82 | 29 | 74 | 1.9 | 26 |
DCM | - | - | 1.8 | 100 | 564 | 12 | 1.9 | 88 | 172 | 15 | 1.9 | 85 |
ACN | - | - | 1.9 | 100 | 104 | 42 | 2.0 | 58 | 90 | 39 | 2.0 | 61 |
MeOH | 28 | 93 | 2.0 | 7 | 111 | 38 | 2.0 | 62 | 5 | 99 | 2.0 | 1 |
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Gutiérrez, M.; Duplouy-Armani, L.; Angiolini, L.; Pintado-Sierra, M.; Sánchez, F.; Douhal, A. Femto- to Millisecond Time-Resolved Photodynamics of a Double-Functionalized Push–Pull Organic Linker: Potential Candidate for Optoelectronically Active MOFs. Int. J. Mol. Sci. 2020, 21, 4366. https://doi.org/10.3390/ijms21124366
Gutiérrez M, Duplouy-Armani L, Angiolini L, Pintado-Sierra M, Sánchez F, Douhal A. Femto- to Millisecond Time-Resolved Photodynamics of a Double-Functionalized Push–Pull Organic Linker: Potential Candidate for Optoelectronically Active MOFs. International Journal of Molecular Sciences. 2020; 21(12):4366. https://doi.org/10.3390/ijms21124366
Chicago/Turabian StyleGutiérrez, Mario, Lucie Duplouy-Armani, Lorenzo Angiolini, Mercedes Pintado-Sierra, Félix Sánchez, and Abderrazzak Douhal. 2020. "Femto- to Millisecond Time-Resolved Photodynamics of a Double-Functionalized Push–Pull Organic Linker: Potential Candidate for Optoelectronically Active MOFs" International Journal of Molecular Sciences 21, no. 12: 4366. https://doi.org/10.3390/ijms21124366