Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization of Quinoxaline-Fused Porphycenes and Their Nickel Complexes
2.2. Protonation of Quinoxaline-Fused Porphycenes and Their Nickel Complexes
3. Materials and Methods
3.1. General Information
3.2. X-ray Crystallography
3.3. Cyclic Voltammetry and Differential Pulse Voltammetry Measurements
3.4. DFT Calculations
3.5. Synthesis of 5,8-Bis(5-hexylthiophen-2-yl)-2,3-di(1H-pyrrol-2-yl)quinoxaline (2a)
3.6. Synthesis of 2,3-Bis(5-bromo-1H-pyrrol-2-yl)-5,8-bis(5-hexylthiophen-2-yl)quinoxaline (3a)
3.7. Synthesis of Di-tert-butyl 5,5′-(5,8-bis(5-hexylthiophen-2-yl)quinoxaline-2,3-diyl) bis(2-bromo-1H-pyrrole-1-carboxylate) (4a)
3.8. Synthesis of Tetra-tert-butyl 5,5″-(5,8-bis(5-hexylthiophen-2-yl)quinoxaline-2,3-diyl) bis(1H,1′H-[2,2′-bipyrrole]-1,1′-dicarboxylate) (5a)
3.9. Synthesis of 2,3-Di(1H,1′H-[2,2′-bipyrrol]-5-yl)-5,8-bis(5-hexylthiophen-2-yl)quinoxaline (6a)
3.10. Synthesis of 5′,5‴-(5,8-Bis(5-hexylthiophen-2-yl)quinoxaline-2,3-diyl)-bis((1H,1′H-[2,2′-bipyrrole]-5-carbaldehyde)) (7a)
3.11. Synthesis of Porphycene 1a-H2
3.12. Synthesis of Porphycene 1a-Ni
3.13. Synthesis of 2,3-Bis(5-bromo-1H-pyrrol-2-yl)-5,8-bis(3,5-dimethoxyphenyl)quinoxaline (3b)
3.14. Synthesis of Di-tert-butyl 5,5′-(5,8-bis(3,5-dimethoxyphenyl)quinoxaline-2,3-diyl) bis(2-bromo-1H-pyrrole-1-carboxylate) (4b)
3.15. Synthesis of Di-tert-butyl 5,5′-(5,8-bis(3,5-dimethoxyphenyl)quinoxaline-2,3-diyl)-bis(2-bromo-1H-pyrrole-1-carboxylate) (5b)
3.16. Synthesis of 2,3-Di(1H,1′H-[2,2′-bipyrrol]-5-yl)-5,8-bis(3,5-dimethoxyphenyl)quinoxaline (6b)
3.17. Synthesis of 5′,5‴-(5,8-Bis(5-hexylthiophen-2-yl)quinoxaline-2,3-diyl) bis((1H,1′H-[2,2′-bipyrrole]-5-carbaldehyde)) (7b)
3.18. Synthesis of Porphycene 1b-H2
3.19. Synthesis of Porphycene 1b-Ni
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples are not available. |
Compound | 1 | 2 | 3 |
---|---|---|---|
Pc | –15.62 | – | – |
1a-H2 | –8.51 | –12.56 | –8.57 |
1b-H2 | –8.57 | –12.67 | –9.03 |
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Kuzuhara, D.; Sakaguchi, M.; Furukawa, W.; Okabe, T.; Aratani, N.; Yamada, H. Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes. Molecules 2017, 22, 908. https://doi.org/10.3390/molecules22060908
Kuzuhara D, Sakaguchi M, Furukawa W, Okabe T, Aratani N, Yamada H. Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes. Molecules. 2017; 22(6):908. https://doi.org/10.3390/molecules22060908
Chicago/Turabian StyleKuzuhara, Daiki, Mika Sakaguchi, Wataru Furukawa, Takuya Okabe, Naoki Aratani, and Hiroko Yamada. 2017. "Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes" Molecules 22, no. 6: 908. https://doi.org/10.3390/molecules22060908