Halogen-bonding has recently emerged as a powerful tool for specific molecular interactions. It is known to be superior to extensively investigated hydrogen-bonding in terms of directionality, hydrophobicity, and tunable binding properties. Orthogonal self-assembly of dipole-dipole interactions and halogen-bonding are interesting combination for constructing functional supramolecular polymeric materials. Herein we have demonstrated the luminescent supramolecular assemblies and co assemblies from three structurally related dipolar naphthalene monoimide (NMI) luminogens (M1, M2 and M3) through underexplored orthogonal dipole–dipole interactions and halogen bonding in the solid state as well as in solution. The different structural motifs of these three dyes are attributed to the variation in the dipolar strength of M1, M2 and M3. Both M1 and M3 are monotopic systems having either halogen bond accepting pyridyl group and halogen bond donating bromine atom (Br), while M2 is a heteroditopic system possessing both the donor and acceptor functionalities. M1 and M3 self assembled through dipole dipole interaction to give 0D nanostructure whereas M2 leads to 1D morphology through synergistic effect of halogen bonding and dipole dipole interactions. Besides that both M1 and M3 can act as chain stoppers for M2 and regulate its morphology via alternate halogen bonding and π-stacking with M2 in the co-assembled state. By varying the feed ratio between M1 and M2, the co-assembly properties could be tuned. The presence of acid labile pyridyl accepter in M1 and M2 offers the opportunity for further structural engineering by halogen bonding with an externally added halogen bond donor (Chol-D) and additionally affords acid-responsive disassembly properties to the resultant luminescent nanostructures. Some of these interesting facets of the afore-mentioned halogen bonded systems will be the topic of this poster presentation.

Orthogonal Halogen Bonding and Dipole-Dipole Interactions Mediated Luminescent Supramolecular Assemblies and Co-assemblies

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27th CRSI National Symposium in Chemistry

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