One “Click” access to self-complementary molecular modules for halogen bonding
G. Cavallo,*a P. Metrangolo,ab T. Pilati,a G. Resnati,a A. Scrivanti,c M. Aversad and E. Cariatie
a NFMLab, Department of Chemistry, Materials, and Chemical Engineering “Giulio Natta”, Politecnico di Milano, Via L. Mancinelli 7, 20131 Milan, Italy
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b VTT-Technical Research Centre of Finland, Biologinkuja 7, 02150 Espoo, Finland
c Dipartimento DSMN, Università Ca'Foscari Venezia, Via Torino 15, I-30172 Mestre, Italy
d Consorzio Interuniversitario CIRCC, Via Ulpiani 27, I-70126 Bari, Italy
e Dipartimento di Chimica and INSTM UdR Milano, University of Milan, via Golgi 19, I-20133 Milan, Italy
RSC Adv., 2016,6, 36723-36727
DOI: 10.1039/C6RA05341F
Received 29 Feb 2016, Accepted 05 Apr 2016
First published online 06 Apr 2016
Novel D–π–A push–pull chromophores were synthesized in good yields by CuAAc coupling of 4-X-2,3,5,6-tetrafluorophenyl-1-azides (X = H, Br, I) with 4-ethynyl-dimethylaniline. Thanks to the self-complementary binding sites at the molecular ends, the iodo derivative self-organizes in the solid state forming head-to-tail halogen-bonded one-dimensional unlimited chains. The second-order NLO properties of the iodo compound have been investigated by the solution-phase electric field induced second-harmonic generation method (EFISH).
