A modular approach towards functionalized highly stable self-complementary quadruple hydrogen bonded systems. Issue 47 (24th November 2017)

• Record Type: Journal Article
• Authors: Rayavarapu, Suresh; Kheria, Sanjeev; Shinde, Dinesh R.; Gonnade, Rajesh G.; Sanjayan, Gangadhar J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 47(2017)
• Page Start: 10087
• Page End: 10094
• Publication Date: 2017-11-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02358h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : This article reports a new class of highly reactive dithiane-tethered self-complementary quadruple hydrogen-bonded systems without having prototropy-related issues. These systems further reacted with different amines to form highly stable molecular duplexes. Abstract : Self-complementary quadruple hydrogen bonded systems have shown potential as key building blocks for developing various supramolecular polymers. Opportunities for the 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 arrays of hydrogen bonding codes are highly stable in non-polar solvents ( K dim > 1.9 × 10 7 M −1 in CDCl3 ) as well as in polar solvents ( K dim > 10 5 in 10% DMSO- d 6 /CDCl3 ). Another notable feature of these self-assembling systems is their insensitivity to prototropy-related issues owing to their prototropic degeneracy, which will enhance their application potential in supramolecular chemistry.