Abstract
A Cu-catalyzed benzannulation reaction transforms ortho(arylene ethynylene) oligomers into ortho-arylenes. This approach circumvents iterative Suzuki cross-coupling reactions previously used to assemble hindered ortho-arylene backbones. These derivatives form helical folded structures in the solid-state and in solution, as demonstrated by X-ray crystallography and solution-state NMR analysis. DFT calculations of misfolded conformations are correlated with variable-temperature 1H and EXSY NMR to reveal that folding is cooperative and more favorable in halide-substituted naphthalenes. Helical ortho-arylene foldamers with specific aromatic sequences organize functional π-electron systems into arrangements ideal for ambipolar charge transport and show preliminary promise for the surface-mediated synthesis of structurally defined graphene nanoribbons.
Original language | English (US) |
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Pages (from-to) | 6357-6364 |
Number of pages | 8 |
Journal | Chemical Science |
Volume | 7 |
Issue number | 10 |
DOIs | |
State | Published - 2016 |
ASJC Scopus subject areas
- Chemistry(all)
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CCDC 1483967: Experimental Crystal Structure Determination
Lehnherr, D. (Creator), Chen, C. (Creator), Pedramrazi, Z. (Creator), Deblase, C. R. (Contributor), Alzola, J. M. (Creator), Keresztes, I. (Creator), Lobkovsky, E. B. (Creator), Crommie, M. F. (Creator) & Dichtel, W. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/ccdc.csd.cc1lt5xh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt5xh&sid=DataCite
Dataset
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CCDC 1483962: Experimental Crystal Structure Determination
Lehnherr, D. (Creator), Chen, C. (Creator), Pedramrazi, Z. (Creator), Deblase, C. R. (Contributor), Alzola, J. M. (Creator), Keresztes, I. (Creator), Lobkovsky, E. B. (Creator), Crommie, M. F. (Creator) & Dichtel, W. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/ccdc.csd.cc1lt5rb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt5rb&sid=DataCite
Dataset
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CCDC 1483964: Experimental Crystal Structure Determination
Lehnherr, D. (Creator), Chen, C. (Creator), Pedramrazi, Z. (Creator), Deblase, C. R. (Contributor), Alzola, J. M. (Creator), Keresztes, I. (Creator), Lobkovsky, E. B. (Creator), Crommie, M. F. (Creator) & Dichtel, W. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/ccdc.csd.cc1lt5td, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt5td&sid=DataCite
Dataset