Supramolecular Gel Based on a Perylene Diimide Dye: Multiple Stimuli Responsiveness, Robustness, and Photofunction

Elisha Krieg, Elijah Shirman, Haim Weissman, Eyal Shimoni, Sharon G. Wolf, Iddo Pinkas§ and Boris Rybtchinski*
Departments of Organic Chemistry, Plant Sciences, and Chemical Research Support, Weizmann Institute of Science, Rehovot 76100, Israel
J. Am. Chem. Soc., 2009, 131 (40), pp 14365–14373
DOI: 10.1021/ja903938g
Publication Date (Web): September 16, 2009
Copyright © 2009 American Chemical Society
boris.rybtchinski@weizmann.ac.il, †

Department of Organic Chemistry.

, ‡

Department of Chemical Research Support.

, §

Department of Plant Sciences.

Abstract

Abstract Image

Design of an extensive supramolecular three-dimensional network that is both robust and adaptive represents a significant challenge. The molecular system PP2b based on a perylene diimide chromophore (PDI) decorated with polyethylene glycol groups self-assembles in aqueous media into extended supramolecular fibers that form a robust three-dimensional network resulting in gelation. The self-assembled systems were characterized by cryo-TEM, cryo-SEM, and rheological measurements. The gel possesses exceptional robustness and multiple stimuli-responsiveness. Reversible charging of PP2b allows for switching between the gel state and fluid solution that is accompanied by switching on and off the material’s birefringence. Temperature triggered deswelling of the gel leads to the (reversible) expulsion of a large fraction of the aqueous solvent. The dual sensibility toward chemical reduction and temperature with a distinct and interrelated response to each of these stimuli is pertinent to applications in the area of adaptive functional materials. The gel also shows strong absorption of visible light and good exciton mobility (elucidated using femtosecond transient absorption), representing an advantageous light harvesting system.

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History

  • Published In Issue October 14, 2009
  • Article ASAPSeptember 16, 2009
  • Received: May 14, 2009

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