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Article

Solution ¹H NMR Confirmation of Folding in Short o-Phenylene Ethynylene Oligomers

Supporting Info

Ticora V. Jones,^† Morris M. Slutsky,^† Roberto Laos,^‡ Tom F. A. de Greef,^§ and Gregory N. Tew*^†

Contribution from Polymer Science & Engineering, University of Massachusetts, Amherst, Massachusetts 01003, Chemistry Department, University of Florida, Gainesville, Florida 32611, and Materials Technology, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands

J. Am. Chem. Soc., 2005, 127 (49), pp 17235–17240

DOI: 10.1021/ja053530+

Publication Date (Web): November 18, 2005

†

University of Massachusetts.

‡

University of Florida.

Eindhoven University of Technology.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tew@mail.pse.umass.edu

Abstract

Oligomers based on an o-phenylene ethynylene (oPE) backbone with polar substituents have been synthesized using Sonogashira methods. Folding of these extremely short oligomers was confirmed via 1D and 2D (NOESY) NMR methods. Utilizing electron-rich and electron-poor phenylene building blocks, variations of these oPE oligomers have been synthesized to determine the folded stability of π-rich vs π-poor vs π-rich−π-poor systems. Slight variations in temperature offer a route, aside from solvent denaturation, to probe the stability of the folded structure. This is the first report of an NMR solution characterization of folding for a PE backbone without hydrogen bonds.

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