@article{081c241c162f41b997ce242e8d7d1e93,
title = "Sequence-defined oligo(: Ortho -arylene) foldamers derived from the benzannulation of ortho (arylene ethynylene)s",
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.",
author = "Dan Lehnherr and Chen Chen and Zahra Pedramrazi and Deblase, {Catherine R.} and Alzola, {Joaquin M.} and Ivan Keresztes and Lobkovsky, {Emil B.} and Crommie, {Michael F.} and Dichtel, {William R.}",
note = "Funding Information: This research was supported by the Army Research Office Multidisciplinary University Research Initiative (MURI) program under grant no. W911NF-15-1-0447 (molecular synthesis and STM imaging), a Beckman Young Investigator Award (to W. R. D.), the NSF (CHE-1124754, structural characterization), and by the US Department of Energy, Office of Basic Energy Sciences Nanomachine Program under contract no. DE-AC02-05CH11231 (molecular deposition). C. R. D. was supported by an NSF GRFP (DGE-1144153). This work made use of the Cornell Center for Materials Research Shared Facilities which are supported through the NSF MRSEC program (DMR-1120296), an NMR spectrometer at Cornell supported by the NSF-MRI program (CHE-1531632), and an 800 MHz NMR instrument at the State University of New York College of Environmental Science and Forestry in Syracuse facilities purchased using NIH grant no. 1S10OD012254-01A1. We thank David Kiemle for his assistance in acquiring the 800 MHz NMR data and Samantha N. MacMillan (X-ray Laboratory, Cornell) for additional X-crystallography presented in the ESI.",
year = "2016",
doi = "10.1039/c6sc02520j",
language = "English (US)",
volume = "7",
pages = "6357--6364",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "10",
}