We are engaged in the synthesis of various fluorinated imines and azobenzenes in order to understand the role of ”Organic Fluorine” in the packing of small organic compounds containing one or more fluorine atoms. Our recent results indicate that the presence of C—F group in small organic molecules can generate various robust supramolecular synthons in the lattice and the replacement of interactive F by Cl and Br alters the crystal structure while the replacement of non-interacting F by Cl or Br do not change the structure or the supramolecular synthon.

The structural analysis of fluorinated azobenzenes also indicated the importance in organic fluorine in crystal engineering.

Our latest studies on fluorinated benzamides (in collaboration with Dr. D. Chopra of IISER Bhopal) and fluorinated phenyl acetamides also indicate that the significance of organic fluorine in crystal engineering even in the presence of strong hydrogen bonds. It has been demonstrated that the fluorine mediated interactions are capable of altering the packing characteristics of molecules, which are mainly associated with each other through strong hydrogen bonds. Generation of various supramolecular synthons involving ”organic fluorine” has been rationalized to understand the influence of organic fluorine in crystal lattice.

The influence of ”organic fluorine” in altering the crystal packing in the absence of strong hydrogen bond but in the presence of weak hydrogen bond has also been investigated by us. Results of this study is currently being communicated for publication.

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