Fluorescence sensing of theobromine by simple 2,6-diamino-pyridine and the novel cyclic chair-like hydrogen-bonded tetramer of its diacetyl derivative

Abstract

2,6-Diaminopyridine is found to be a simple fluorescent sensor for theobromine and its diacetyl derivative 2 also effectively binds theobromine. The receptor-binding sites are based on the co-operative hydrogen-bonding abilities of secondary amides. An unprecedented hydrogen-bonded self-organised cyclic tetrameric supramolecular network is shown for one such small molecule 2 containing one heterocyclic ring in contrast to the binuclear substrates like guanine or pterin which usually form cyclic tetrameric structures.