Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3′,4,4′-Tetraethyl-5,5′-divinyl-2,2′-bipyrrole Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Nuclear Magnetic Resonance (NMR) Spectroscopy
2.3. Crystal Structure
2.4. UV-Vis Absorption and Photoluminescence
2.5. TD-DFT Calculations
3. Experimental
3.1. Materials and Instruments
3.2. X-ray Crystallography
3.3. Synthesis
3.4. Computational Methods
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Compounds | λAbs (nm) | λFL (nm) | ΦFL (−) |
---|---|---|---|
1 | 355 | 414 | NA a |
2 | 499, 531 | 553 | 0.05 |
3 | 555 | 576 | 0.81 |
4 | 582 | 602 | 0.93 |
4Me [22] | 569 | 578 | 0.88 |
Compounds | λAbs (Obs.) (nm) | λAbs (Calcd.) (nm) | Transitions | Oscillator Strength |
---|---|---|---|---|
1 | 355 | 403.31 | 81(HOMO)‒82(LUMO) | 1.0825 |
2 | 499, 531 | 556.11 | 104(HOMO−1)‒107(LUMO+1) 105(HOMO)‒106(LUMO) | 1.5891 |
3 | 555 | 553.40 | 146(HOMO−1)‒149(LUMO+1) 147(HOMO)‒148(LUMO) | 1.7047 |
4 | 582 | 574.31 | 152(HOMO−1)‒155 (LUMO+1) 153(HOMO)‒154(LUMO) | 1.8560 |
4Me | 569 | 560.00 | 128(HOMO−1)‒131(LUMO+1) 129(HOMO)‒130(LUMO) | 1.9396 |
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Okawara, T.; Kawano, R.; Morita, H.; Finkelstein, A.; Toyofuku, R.; Matsumoto, K.; Takehara, K.; Nagamura, T.; Iwasa, S.; Kumar, S. Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3′,4,4′-Tetraethyl-5,5′-divinyl-2,2′-bipyrrole Derivatives. Molecules 2017, 22, 1816. https://doi.org/10.3390/molecules22111816
Okawara T, Kawano R, Morita H, Finkelstein A, Toyofuku R, Matsumoto K, Takehara K, Nagamura T, Iwasa S, Kumar S. Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3′,4,4′-Tetraethyl-5,5′-divinyl-2,2′-bipyrrole Derivatives. Molecules. 2017; 22(11):1816. https://doi.org/10.3390/molecules22111816
Chicago/Turabian StyleOkawara, Toru, Reo Kawano, Hiroya Morita, Alan Finkelstein, Renjiro Toyofuku, Kanako Matsumoto, Kenji Takehara, Toshihiko Nagamura, Seiji Iwasa, and Sanjai Kumar. 2017. "Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3′,4,4′-Tetraethyl-5,5′-divinyl-2,2′-bipyrrole Derivatives" Molecules 22, no. 11: 1816. https://doi.org/10.3390/molecules22111816