01705nas a2200181   4500008004100000022001400041245004500055210004400100260007100144300001400215490000700229520112000236100002401356700002401380700002101404700002101425856007701446       2005                        eng d  a0022-326300aSelf-assembly with degenerate prototropy0 aSelfassembly with degenerate prototropy  a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcAUG  a6461-64670 v703 a<p>This work describes a rational approach for addressing the prototropy-related problems in heterocycle-based self-assembling systems by the use of degenerate prototropy. As a proof of principle, the utility of degenerate prototropy is demonstrated herein by developing heterocycle-based AADD-type self-assembling modules that exist as ``single set of protameric pair (duplex)'' in both solution and solid states. These self-assembling modules are quickly accessible in good yield by reacting 2-amino-5,5-disubstituted-1H-pyrimidine-4,6-diones, available in one step by the condensation of (x,a-dialkyl malonates and free guanidine, with isocyanates. Evidence from NMR spectroscopy, ESI mass spectrometry, and single-crystal X-ray diffraction studies confirmed the formation of molecular duplexes. The effect of electronic repulsion in duplex formation is also investigated. Their ready synthetic accessibility, remarkably high propensity to crystal formation, and the novel property of degenerate prototropy would make these novel self-assembling molecules promising candidates for many proposed applications.</p>1 aBaruah, Pranjal, K.1 aGonnade, Rajesh, G.1 aPhalgune, U., D.1 aSanjayan, G., J.  uhttps://library.ncl.res.in/content/self-assembly-degenerate-prototropy-1