Halogen bonding modulates hydrogel formation from Fmoc amino acids
A. Pizzi,[a] L. Lascialfari,[a] N. Demitri,[b] A. Bertolani,[a] D. Maiolo,[a] E. Carretti,[d] P. Metrangolo*[a,c]
a. Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials and Chemical Engineering“Giulio Natta”, Politecnico di Milano, Via L. Mancinelli 7, I-20131 Milano, Italy.
b. Elettra-Synchrotron Light Source, S.S. 14 Km 163.5, Area Science Park, 34149 Basovizza, Trieste, Italy.
c. Department of Applied Physics, Aalto University, Puumiehenkuja 2, Espoo, FI-02150, Finland.
d. CSGI & Department of Chemistry “Ugo Schiff”, Università di Firenze, Firenze, Italy
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The single crystal X-ray structures of a series of p-halogenated Fmoc-phenylalanines highlight the role of halogen bonding in their supramolecular organization in the solid state. The amino acids showing the occurrence of halogen bonding resulted in gels with the strongest mechanical properties. All gelation parameters could be ranked according to halogen atom polarizability, i.e., halogen bond strength.
