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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



Publikationsverlauf

Eingereicht: 10. Mai 2022

Angenommen nach Revision: 09. Juni 2022

Accepted Manuscript online:
10. Juni 2022

Artikel online veröffentlicht:
29. Juni 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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  • References

    • 1a Khan FI, Kr Ghoshal A. J. Loss Prev. Process Ind. 2000; 13: 527
      CrossrefPubMed
    • 1b Pinalli R, Pedrini A, Dalcanale E. Chem. Eur. J. 2018; 24: 1010
      CrossrefPubMed
    • 1c Lubczyk D, Hahma A, Brutschy M, Siering C, Waldvogel SR. Propellants, Explos. Pyrotech. 2015; 40: 590
      CrossrefPubMed
  • 2 Ryvlin D, Girschikofsky M, Schollmeyer D, Hellmann R, Waldvogel SR. Global Challenges 2018; 2: 1800057
    CrossrefPubMed
  • 3 Gimeno P, Besacier F, Bottex M, Dujourdy L, Chaudron-Thozet H. Forensic Sci. Int. 2005; 155: 141
    CrossrefPubMed
  • 4 Brutschy M, Schneider MW, Mastalerz M, Waldvogel SR. Chem. Commun. 2013; 49: 8398
    CrossrefPubMed
    • 5a Baur X, Ollesch T, Poschadel B, Budnik LT, Finger G SMatz. Zbl. Arbeitsmed. 2007; 57: 89
      CrossrefPubMed
    • 5b Zampolli S, Elmi I, Mancarella F, Betti P, Dalcanale E, Cardinali GC, Severi M. Sens. Actuators, B 2009; 141: 322
      CrossrefPubMed
    • 5c Zampolli S, Betti P, Elmi I, Dalcanale E. Chem. Commun. 2007; 27: 2790
      CrossrefPubMed
    • 5d Clément P, Korom S, Struzzi C, Parra EJ, Bittencourt C, Ballester P, Llobet E. Adv. Funct. Mater. 2015; 25: 4011
      CrossrefPubMed
    • 5e Dickert FL, Lieberzeit P, Miarecka SG, Mann KJ, Hayden O, Palfinger C. Biosens. Bioelectron. 2004; 20: 1040
      CrossrefPubMed
  • 6 Lynch KL. Mass Spectrometry for the Clinical Laboratory. Amsterdam: Elsevier; 2017
    Google Scholar
    • 7a Wu C, Steiner WE, Tornatore PS, Matz LM, Siems WF, Atkinson DA, Hill HH. Talanta 2002; 57: 123
      CrossrefPubMed
    • 7b Mäkinen MA, Anttalainen OA, Sillanpää MET. Anal. Chem. 2010; 82: 9594
      CrossrefPubMed
  • 8 Oprea A, Weimar U. Anal. Bioanal. Chem. 2019; 411: 1761
    CrossrefPubMed
  • 9 Oprea A, Weimar U. Anal. Bioanal. Chem. 2020; 412: 6707
    CrossrefPubMed
    • 10a Brutschy M, Schneider MW, Mastalerz M, Waldvogel SR. Adv. Mater. 2012; 24: 6049
      CrossrefPubMed
    • 10b Brutschy M, Stangenberg R, Beer C, Lubczyk D, Baumgarten M, Müllen K, Waldvogel SR. ChemPlusChem 2015; 80: 54
      CrossrefPubMed
    • 10c Xu T, Xu P, Zheng D, Yu H, Li X. Anal. Chem. 2016; 88: 12234
      CrossrefPubMed
    • 10d Girschikofsky M, Rosenberger M, Belle S, Brutschy M, Waldvogel SR, Hellmann R. Proc. SPIE–Int. Soc. Opt. Eng. 2012; 8439: 843916
      PubMed
    • 10e Börner S, Orghici R, Waldvogel SR, Willer U, Schade W. Appl. Opt. 2009; 48: B183
      CrossrefPubMed
    • 10f Orghici R, Willer U, Gierszewska M, Waldvogel SR, Schade W. Appl. Phys. B 2008; 90: 355
      CrossrefPubMed
    • 10g Orghici R, Lützow P, Burgmeier J, Koch J, Heidrich H, Schade W, Welschoff N, Waldvogel S. Sensors 2010; 10: 6788
      CrossrefPubMed
  • 11 Brutschy M, Lubczyk D, Müllen K, Waldvogel SR. Anal. Chem. 2013; 85: 10526
    CrossrefPubMed
  • 12 Prantl E, Kohl B, Ryvlin D, Biegger P, Wadepohl H, Rominger F, Bunz UHF, Mastalerz M, Waldvogel SR. ChemPlusChem 2019; 13: 1239
    CrossrefPubMed
  • 13 Wessels A, Klöckner B, Siering C, Waldvogel SR. Sensors 2013; 13: 12012
    CrossrefPubMed
    • 14a Mujahid A, Afzal A, Dickert FL. Sensors 2019; 19: 4395
      CrossrefPubMed
    • 14b Linke A, Jungbauer SH, Huber SM, Waldvogel SR. Chem. Commun. 2015; 51: 2040
      CrossrefPubMed
    • 15a Lubczyk D, Siering C, Lörgen J, Shifrina ZB, Müllen K, Waldvogel SR. Sens. Actuators, B 2010; 143: 561
      CrossrefPubMed
    • 15b Lubczyk D, Grill M, Baumgarten M, Waldvogel SR, Müllen K. ChemPlusChem 2012; 77: 102
      CrossrefPubMed
    • 16a Kohl B, Bohnwagner MV, Rominger F, Wadepohl H, Dreuw A, Mastalerz M. Chem. Eur. J. 2016; 22: 646
      CrossrefPubMed
    • 16b Kohl B, Rominger F, Mastalerz M. Org. Lett. 2014; 16: 704
      CrossrefPubMed
    • 16c Kohl B, Rominger F, Mastalerz M. Chem. Eur. J. 2015; 21: 17308
      CrossrefPubMed
  • 17 Dickert FL, Bäumler UPA, Stathopulos H. Anal. Chem. 1997; 69: 1000
    CrossrefPubMed
  • 18 Schaub TA, Prantl EA, Kohn J, Bursch M, Marshall CR, Leonhardt EJ, Lovell TC, Zakharov LN, Brozek CK, Waldvogel SR, Grimme S, Jasti R. J. Am. Chem. Soc. 2020; 142: 8763
    CrossrefPubMed
  • 19 Bunz UHF, Freudenberg J. Acc. Chem. Res. 2019; 52: 1575
    CrossrefPubMed
  • 20 Hahn S, Alrayyani M, Sontheim A, Wang X, Rominger F, Miljanić OŠ, Bunz UHF. Chem. Eur. J. 2017; 23: 10543
    CrossrefPubMed
  • 21 Hahn S, Koser S, Hodecker M, Seete P, Rominger F, Miljanić OŠ, Dreuw A, Bunz UHF. Chem. Eur. J. 2018; 24: 6968
    CrossrefPubMed
  • 22 Goddard TD, Huang CC, Meng EC, Pettersen EF, Couch GS, Morris JH, Ferrin TE. Protein Sci. 2018; 27: 14
    CrossrefPubMed
  • 23 Pettersen EF, Goddard TD, Huang CC, Meng EC, Couch GS, Croll TI, Morris JH, Ferrin TE. Protein Sci. 2021; 30: 70
    CrossrefPubMed
    • 24a Abbott LJ, McKeown NB, Colina CM. J. Mater. Chem. A 2013; 1: 11950
      CrossrefPubMed
    • 24b Abbott LJ, McDermott AG, Del Regno A, Taylor RGD, Bezzu CG, Msayib KJ, McKeown NB, Siperstein FR, Runt J, Colina CM. J. Phys. Chem. B 2013; 117: 355
      CrossrefPubMed
    • 24c Taylor RGD, Bezzu CG, Carta M, Msayib KJ, Walker J, Short R, Kariuki BM, McKeown NB. Chem. Eur. J. 2016; 22: 2466
      CrossrefPubMed
  • 25 Fenn JB. Angew. Chem. Int. Ed. Engl. 2003; 42: 3871
    CrossrefPubMed
  • 26 Fenn JB. Angew. Chem. 2003; 115: 3999
    CrossrefPubMed
  • 27 Heil C, Windscheif G, Braschohs S, Flörke J, Gläser J, Lopez M, Müller-Albrecht J, Schramm U, Bargon J, Vögtle F. Sens. Actuators, B 1999; 61: 51
    CrossrefPubMed
  • 28 Wortmann A, Kistler-Momotova A, Zenobi R, Heine MC, Wilhelm O, Pratsinis SE. J. Am. Soc. Mass Spectrom. 2007; 18: 385
    CrossrefPubMed
  • 29 Neubig B, Briese W. Das große Quarzkochbuch. Quarze, Quarzoszillatoren, Quarz- und Oberflächenwellenfilter (SAW), Meßtechnik. Feldkirchen: Franzis; 1997
    Google Scholar
  • 30 Masel RI. Principles of Adsorption and Reaction on Solid Surfaces. New York: Wiley; 1996
    Google Scholar
  • 31 Pyka I, Ryvlin D, Waldvogel SR. ChemPlusChem 2016; 81: 926
    CrossrefPubMed
  • 32 Bannwarth C, Ehlert S, Grimme S. J. Chem. Theory Comput. 2019; 15: 1652
    CrossrefPubMed
  • 33 Grimme S, Bannwarth C, Caldeweyher E, Pisarek J, Hansen A. J. Chem. Phys. 2017; 147: 161708
    CrossrefPubMed
  • 34 Grimme S, Bannwarth C, Shushkov P. J. Chem. Theory Comput. 2017; 13: 1989
    CrossrefPubMed
  • 35 Atwood JL, Barbour LJ, Jerga A, Schottel BL. Science 2002; 298: 1000
    CrossrefPubMed
  • 36 Swist M, Wilamowski J, Parczewski A. Forensic Sci. Int. 2005; 155: 100
    CrossrefPubMed