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A Modular Approach Towards Functionalized Highly Stable Self-complementary Quadruple Hydrogen Bonded Systems

Abstract

Self-complementary quadruple hydrogen bonded systems have shown potential as key building blocks for developing various supramolecular polymers. Opportunities for introduction of multiple functionalities would further augment, in principle, their application potential. Herein, we report a novel modular approach to simultaneously introduce two closely aligned side chains into AADD-type self-complementary quadruple hydrogen-bonding systems. Dithiane-tethered ureidopyrimidinone has been used as a reactive intermediate to efficiently attach closely aligned side chains by simply reacting with amines to form highly stable molecular duplexes. These duplexes featuring AADD-type array of hydrogen bonding codes are highly stable in non-polar solvent (Kdim > 1.9 x 107 M-1 in CDCl3) as well as in polar solvent (Kdim > 105 in 10% DMSO-d6/CDCl3). Another notable feature of these self-assembling systems is their insensitivity to prototropy-related issues owing to prototropic degeneracy, which will enhance their application potential in supramolecular chemistry.

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Publication details

The article was received on 21 Sep 2017, accepted on 09 Nov 2017 and first published on 09 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02358H
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    A Modular Approach Towards Functionalized Highly Stable Self-complementary Quadruple Hydrogen Bonded Systems

    S. Rayavarapu, S. Kheria, D. R. Shinde, R. G. Gonnade and G. J. Sanjayan, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB02358H

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