Weak interactions dominating the supramolecular self-assembly in a salt: a designed single-crystal-to-single-crystal topochemical polymerization of a terminal aryldiacetylene

Journal of the American Chemical Society
Zhong LiJoseph W Lauher

Abstract

Single-crystal-to-single-crystal (SCSC) topochemical polymerizations of diacetylenes can yield nearly defect-free conjugated polymer crystals unattainable by other methods. Aryl-substituted diacetylenes with their potentially greater conjugation have been targeted for years, but until now no one has reported a SCSC polymerization of any aryl-substituted diacetylene. This is presumably due to the rigidity of such diaryl-substituted monomers as well as the lack of control over the supramolecular structure. To address this problem, the polymerization of a terminal phenyldiacetylene was targeted. It was assumed that a terminal diacetylene should demonstrate greater flexibility in the solid state. To establish the necessary (approximately 4.9 A) repeat distance, commensurate with the repeat distance in the polymer, a host-guest system was designed. The chosen diacetylene guest, the amine DABzNH(2), was to be crystallized with the oxalamide dicarboxylic acid host, H(2)og. The plan required a segregation of the hydrogen bonds, amide-amide hydrogen bonds to establish the 4.9 A spacing, and the carboxylate to ammonium ion hydrogen bonds to organize the guest. Prior to carrying out the diacetylene synthesis a series of model salts were s...Continue Reading

References

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Citations

Apr 19, 2016·Journal of the American Chemical Society·Mitsuharu SuzukiYves Rubin
Oct 30, 2016·Journal of the American Chemical Society·Baiju P KrishnanKana M Sureshan
Aug 23, 2017·Chemical Communications : Chem Comm·Madushani DharmarwardanaJeremiah J Gassensmith
Nov 22, 2018·Angewandte Chemie·Vignesh Athiyarath, Kana M Sureshan
Oct 11, 2014·Organic & Biomolecular Chemistry·Isabelle LevesqueJean-François Morin
Jul 22, 2014·Angewandte Chemie·Atchutarao Pathigoolla, Kana M Sureshan
Sep 1, 2012·Chemical Communications : Chem Comm·Jules Roméo NéaboJean-François Morin
Jul 3, 2013·Angewandte Chemie·Atchutarao Pathigoolla, Kana M Sureshan
Feb 6, 2021·Chemical Society Reviews·Kuntrapakam HemaKana M Sureshan
Apr 21, 2010·Organic Letters·Mitsuharu SuzukiYves Rubin
Feb 23, 2011·Organic Letters·Jules Roméo NéaboJean-Francois Morin
Sep 14, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Audithya NyayachavadiSimon Rondeau-Gagné
Oct 22, 2011·Journal of the American Chemical Society·Eric L SpitlerWilliam R Dichtel
Dec 16, 2011·Journal of the American Chemical Society·Te-Jung HsuJoseph W Lauher
May 3, 2019·The Journal of Organic Chemistry·Danny C LenstraJasmin Mecinović
Nov 13, 2010·The Journal of Organic Chemistry·Thanh LuuRik R Tykwinski
Dec 22, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Britta E I RamakersDennis W P M Löwik
Aug 2, 2019·Accounts of Chemical Research·Racquel C DeCiccoNancy S Goroff

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