Triptycene-Roofed Quinoxaline Cavitands for the Supramolecular Detection of BTEX in Air

Federico Bertani; Nicolò Riboni; Federica Bianchi; Giovanna Brancatelli; Elizabeth S Sterner; Roberta Pinalli; Silvano Geremia; Timothy M Swager; Enrico Dalcanale

doi:10.1002/chem.201504229

Triptycene-Roofed Quinoxaline Cavitands for the Supramolecular Detection of BTEX in Air

Chemistry. 2016 Mar 1;22(10):3312-3319. doi: 10.1002/chem.201504229. Epub 2016 Jan 13.

Authors

Federico Bertani^{1

2}, Nicolò Riboni¹, Federica Bianchi¹, Giovanna Brancatelli³, Elizabeth S Sterner², Roberta Pinalli¹, Silvano Geremia³, Timothy M Swager⁴, Enrico Dalcanale⁵

Affiliations

¹ Department of Chemistry, University of Parma, Parco Area delle Scienze 17A, Parma, 43124, Italy.
² Department of Chemistry, Massachusetts Institute of Technology, 77 Mass Avenue, 02139, Cambridge, MA, USA.
³ Department of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgeri 1, 34127, Trieste, Italy.
⁴ Department of Chemistry, Massachusetts Institute of Technology, 77 Mass Avenue, 02139, Cambridge, MA, USA. tswager@mit.edu.
⁵ Department of Chemistry, University of Parma, Parco Area delle Scienze 17A, Parma, 43124, Italy. enrico.dalcanale@unipr.it.

PMID: 26762207
DOI: 10.1002/chem.201504229

Abstract

Two novel triptycene quinoxaline cavitands (DiTriptyQxCav and MonoTriptyQxCav) have been designed, synthesized, and applied in the supramolecular detection of benzene, toluene, ethylbenzene, and xylenes (BTEX) in air. The complexation properties of the two cavitands towards aromatics in the solid state are strengthened by the presence of the triptycene moieties at the upper rim of the tetraquinoxaline walls, promoting the confinement of the aromatic hydrocarbons within the cavity. The two cavitands were used as fiber coatings for solid-phase microextraction (SPME) BTEX monitoring in air. The best performances in terms of enrichment factors, selectivity, and LOD (limit of detection) values were obtained by using the DiTriptyQxCav coating. The corresponding SPME fiber was successfully tested under real urban monitoring conditions, outperforming the commercial divinylbenzene-Carboxen-polydimethylsiloxane (DVB-CAR-PDMS) fiber in BTEX adsorption.

Keywords: cavitands; environmental monitoring; host-guest systems; solid-phase microextraction; volatile organic compounds.