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.

Saccone M., Dichiarante V., Forni A., Goulet-Hanssens A., Cavallo G., Vapaavuori J., et al. (2015). Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning. JOURNAL OF MATERIALS CHEMISTRY. C, 3(4), 759-768 [10.1039/c4tc02315c].

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

Saccone M.
Supervision
;
2015-01-01

Abstract

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.
2015
Settore CHIM/07 - Fondamenti Chimici Delle Tecnologie
Saccone M., Dichiarante V., Forni A., Goulet-Hanssens A., Cavallo G., Vapaavuori J., et al. (2015). Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning. JOURNAL OF MATERIALS CHEMISTRY. C, 3(4), 759-768 [10.1039/c4tc02315c].
File in questo prodotto:
File Dimensione Formato  
Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning.pdf

accesso aperto

Descrizione: Articolo open access
Tipologia: Versione Editoriale
Dimensione 1.3 MB
Formato Adobe PDF
1.3 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/398653
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 86
  • ???jsp.display-item.citation.isi??? 83
social impact