Design and Synthesis of Cofacially-Arrayed Polyfluorene Wires for Electron and Energy Transfer Studies
Abstract
:1. Introduction
2. Cyclophanes as Models for the Study of π-Stacking
3. Multi-Decker Cyclophanes
4. Rationale for the Design of a New Class of Cofacially π-Stacked Polyfluorenes
5. Development of Synthetic Strategies for the Preparation of π-Stacked Polyfluorene Oligomers
6. Demonstration of the Cofaciality of the Fluorene Rings in F1–F6 by 1H NMR Spectroscopy
7. X-ray Crystallography of the π-Stacked Polyfluorenes
8. Electronic and Emission Spectroscopy of Polyfluorenes
9. Electrochemistry/Photoelectron Spectroscopy of Polyfluorenes
10. Generation and Spectroscopy of Polyfluorene Cation Radicals
11. Generation of Polyfluorene Anion Radicals and Study of Charge Delocalization by EPR Spectroscopy
12. Donor–Spacer–Acceptor Triads with Polyfluorenes as Spacers and Demonstration of the Triplet Energy Transfer
13. Materials and Methods
13.1. Preparation of 9,9-Bis-(2-methyl-allyl)-9H-fluorene (42)
13.2. Preparation of 1-[9-(2-Oxo-propyl)-9H-fluoren-9-yl]propan-2-one (43)
13.3. Preparation of 2-Biphenyl-2-yl-1-[9-(2-biphenyl-2-yl-2-hydroxy-propyl)-9H-fluoren-9-yl]propan-2-ol (44)
13.4. Preparation of 9-Methyl-9H-fluorene (45)
13.5. Preparation of 2,3-Bis(9-methylfluorene)methylpropene (46)
13.6. Preparation of 1,3-Bis(9-methyl-9H-fluoren-9-yl)propan-2-one (47)
13.7. Preparation of 2-Biphenyl-2-yl-1,3-bis(9-methyl-9-H-fluoren-9-yl)propan-2-ol (48)
13.8. Preparation of 9-[(Fluoren-9-yl)-methyl]flourene (55)
13.9. Preparation of 9,9-Bis((9H-fluoren-9-yl)methyl)-9H-fluorene (63)
13.10. Preparation of Bis(9-((9H-fluoren-9-yl)methyl)-9H-fluoren-9-yl)methane (64)
13.11. Preparation of 9-Methyl-9H-fluorene-d9 (70)
13.12. Preparation of 9-(2-Bromoallyl)-9-methyl-9H-fluorene-d8 (71)
13.13. Preparation of 9-(2-Biphenyl-2-yl-allyl)-9-methyl-9H-fluorene-d8 (72)
13.14. Preparation of Bis(9-methyl-9H-fluoren-9-yl)methane-d8 (F2-d8)
13.15. Preparation of Di(9H-fluoren-9-yl)methane-d16 (73)
13.16. Preparation of 9,9-Bis-(2-bromo-allyl)-9H-fluorene-d8 (74)
13.17. Preparation of 9,9-Bis(2-biphenyl-2-yl-allyl)-9H-fluorene-d8 (75)
13.18. Preparation of 9,9-Bis((9-methyl-9H-fluoren-9-yl)methyl)-9H-fluorene-d8 (F3-d8)
13.19. Preparation of 9-(2-Bromo-allyl)-9-[(9-(2-bromo-allyl)-fluoren-9-yl)methyl]fluorene-d16 (76)
13.20. Preparation of 9-(2-Biphenyl-2-yl-allyl)-9-[(9-(2-biphenyl-2-yl-allyl)fluoren-9-yl)methyl]fluorene-d16 (77)
13.21. Preparation of Bis(9-((9-methyl-9H-fluoren-9-yl)methyl)-9H-fluoren-9-yl)methane-d16 (F4-d16)
14. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Conflicts of Interest
References
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Monomer | Eox (V) a | Cyclophane | Eox (V) a | D (V) | |
---|---|---|---|---|---|
23 | 0.66 | 0.33 | 0.33 | ||
24 | 0.73 | 0.35 | 0.38 | ||
26 | 0.77 | 0.42 | 0.35 | ||
27 | 0.82 | 0.57 | 0.25 |
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Rathore, R.; Abdelwahed, S.H. Design and Synthesis of Cofacially-Arrayed Polyfluorene Wires for Electron and Energy Transfer Studies. Molecules 2023, 28, 3717. https://doi.org/10.3390/molecules28093717
Rathore R, Abdelwahed SH. Design and Synthesis of Cofacially-Arrayed Polyfluorene Wires for Electron and Energy Transfer Studies. Molecules. 2023; 28(9):3717. https://doi.org/10.3390/molecules28093717
Chicago/Turabian StyleRathore, Rajendra, and Sameh H. Abdelwahed. 2023. "Design and Synthesis of Cofacially-Arrayed Polyfluorene Wires for Electron and Energy Transfer Studies" Molecules 28, no. 9: 3717. https://doi.org/10.3390/molecules28093717