Extended supramolecular organization of π-systems using yet unexplored simultaneous intra- and inter-molecular H-bonding motifs of 1,3-dihydroxy derivativesElectronic supplementary information (ESI) available: Synthesis and additional characterization data. See DOI: 10.1039/c4cc10335a

Unique H-bonding motifs of 1,3-dihydroxyl derivatives involving simultaneous intra- and inter-molecular H-bonding results in extended organization of pendant chromophores with a spatial distance suitable for π-π interaction. A preformed assembly with appended acceptor units exhibits host-guest interaction with specific donors by charge-transfer complex formation. Simultaneous intra- and inter-molecular H-bonding among 1,3-dihydroxyl derivatives with acceptor chromophores leads to fibrillar gelation facilitating π-stacking and specific donor intercalation.