Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning

Marco Saccone, Valentina Dichiarante, Giancarlo Terraneo, Jaana Vapaavuori, Alessandra Forni, Alexis Goulet-Hanssens, Marco Saccone, Pierangelo Metrangolo, Giuseppe Resnati, Christopher J. Barrett, Gabriella Cavallo, Arri Priimagi

Research output: Contribution to journalArticlepeer-review

68 Citations (Scopus)


Halogen bonding, a noncovalent interaction possessing several unique features compared to the more familiar hydrogen bonding, is emerging as a powerful tool in functional materials design. Herein, we unambiguously show that one of these characteristic features, namely high directionality, renders halogen bonding the interaction of choice when developing azobenzene-containing supramolecular polymers for light-induced surface patterning. The study is conducted by using an extensive library of azobenzene molecules that differ only in terms of the bond-donor unit. We introduce a new tetrafluorophenol-containing azobenzene photoswitch capable of forming strong hydrogen bonds, and show that an iodoethynyl-containing azobenzene comes out on top of the supramolecular hierarchy to provide unprecedented photoinduced surface patterning efficiency. Specifically, the iodoethynyl motif seems highly promising in future development of polymeric optical and photoactive materials driven by halogen bonding.
Original languageEnglish
Pages (from-to)759-768
Number of pages10
Publication statusPublished - 2015

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Materials Chemistry

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