title: Three in one: prototropy-free highly stable AADD-type self-complementary quadruple hydrogen-bonded molecular duplexes with a built-in fluorophore.
abstract: This communication reports an effective approach for addressing the prototropy-related problems in heterocycle-based AADD-type self-assembling systems by freezing their hydrogen-bonding codes, by utilizing intramolecular bifurcated hydrogen bonding interactions. Using this strategy, we have also developed a hydroquinone-conjugated AADD-type self-assembling system adorned with three valuable features such as prototropy-free dimerization yielding single duplexes, high duplex stability and a built-in fluorophore, which would augment its application potential. The rational approach used herein to arrest prototropic shift may also find application elsewhere, wherein proton shift-mediated structural changes become a detrimental factor.
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr Homi Bhabha Road, Pune-411008, India. gj.sanjayan@ncl.res.in.
authors.forename: Sanjeev
authors.initials: S
authors.lastname: Kheria
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr Homi Bhabha Road, Pune-411008, India. gj.sanjayan@ncl.res.in.
authors.forename: Suresh
authors.initials: S
authors.lastname: Rayavarapu
authors.affiliation: Central NMR Facility, CSIR-National Chemical Laboratory (CSIR-NCL), Dr Homi Bhabha Road, Pune-411008, India.
authors.forename: Amol S
authors.initials: AS
authors.lastname: Kotmale
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr Homi Bhabha Road, Pune-411008, India. gj.sanjayan@ncl.res.in.
authors.forename: Gangadhar J
authors.identifier: http://orcid.org/0000-0001-7764-7329
authors.initials: GJ
authors.lastname: Sanjayan