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CC BY-NC-ND 4.0 · Organic Materials 2022; 4(02): 36-42
DOI: 10.1055/a-1873-5186
Supramolecular Chemistry
Original Article

Experimental and Computational Studies of Phenylene-Bridged Azaacenes as Affinity Materials for Sensing Using Quartz Crystal Microbalances

Ephraim Prantl
a   Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10 – 14, 55128 Mainz, Germany
,
Sebastian Hahn
b   Institute of Organic Chemistry, Ruprecht Karl University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Uwe H. F. Bunz 
b   Institute of Organic Chemistry, Ruprecht Karl University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Siegfried R. Waldvogel 
a   Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10 – 14, 55128 Mainz, Germany
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Abstract

Phenylene-bridged, TIPS-alkynylated azaacenes are excellent materials for selective gas sorption. In this study, we utilized 195 MHz high-fundamental-frequency quartz crystal microbalances, coated with cyclic azaacenes, and determined their affinity towards hazardous and narcotics-related compounds such as benzene, γ-butyrolactone (GBL) or safrole. Computational investigations by extended tight binding intermolecular force field allowed better understanding of the determined unique features. Remarkable selective affinities were found towards GBL and safrole – both dangerous compounds which can be abused as precursors for narcotics. With these systematic approaches, we were able to get a better insight into the selective adsorption and how to design better affinity materials

Key words

affinity materials - quartz crystal microbalances - sensors - azaacene - trace analysis

Supporting Information



Publication History

Received: 10 May 2022

Accepted after revision: 09 June 2022

Accepted Manuscript online:
10 June 2022

Article published online:
29 June 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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