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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Hydrogen-Bonded Oligoamide Duplexes as Programmable Molecular Recognition Units: A Systematic Approach Towards Directed Self-Assembly and Controlled Non-Covalent Synthesis

Author(s): Lihua Yuan, Penghui Zhang, Wen Feng and Bing Gong

Volume 15, Issue 9, 2011

Page: [1250 - 1265] Pages: 16

DOI: 10.2174/138527211795378236

Price: $65


Association units with high strength and specificity are getting increasing attention in the construction of well-defined selfassembling systems, which are making controlled non-covalent synthesis a reality. A class of hydrogen-bonded duplexes consisting of oligoamide strands carrying various combinations (sequences) of hydrogen-bond donors and acceptors has exhibited superb ability as intermolecular association units. These duplexes are featured by programmable sequence-specificity, predictable binding strength, ready synthetic availability and modifiability. With association constants ranging from ∼104 to 109M-1, these hydrogen-bonded duplexes offer a diverse set of association units capable of specifying intermolecular association in a controlled and directed manner. The efficacy of these molecules as molecular assembler has already been demonstrated by a number of examples such as the construction of supramolecular block copolymers, the templation of β-sheets, directed chemical reactions such as olefin metathesis and disulfide exchange. By integrating hydrogen bonding with dynamic covalent interactions, covalently linked duplexes are formed sequence-specifically in a selfassembling fashion in highly competitive media, which represents a major progress in creating association units combining the strength of covalent bonds and the specificity of multiple hydrogen bonds. Recently, hydrogen-bonded and/or covalent crosslinked duplexes have been found to serve as gelators for organic solvents, which may open a new avenue for developing novel materials.

Keywords: Hydrogen-bonded duplex, oligoamide strand, association unit, multiple hydrogen bonds, sequence-specificity, non-covalent interactions, self-assembly, supramolecular polymer, hydrogen bonding, stacking, electrostatic, van der Waals, hydrophobic forces, homo-duplexes, hetero-duplexes

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