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  • Reversible

    Self-Assembled Monolayers

    as Biosensor Platforms

    Dissertation

    by

    Annabell Tenboll

    from Marl

    In Partial Fulfillment of the

    Requirements for the Degree

    Doctor of Chemistry

    (Dr. rer. nat.)

    Department of Chemistry

    University Duisburg-Essen

    June 2013

  • Die vorliegende Arbeit wurde im Zeitraum von April 2011 bis Juni 2013 im Arbeitskreis

    von Priv. - Doz. Dr. Börje Sellergren am Institut für Umweltforschung der Technischen

    Universität Dortmund angefertigt.

    Gutachter: Prof. Dr. Thomas Schrader

    Prof. Dr. Börje Sellergren

    Vorsitzender: Prof. Dr. Stephan Schulz

    Tag der Disputation: 11. September 2013

  • meiner Mutter Anna-Maria und meinem Freund Domenic

  • Table of content Summary………………………………………………………………………………..I

    Zusammenfassung…………………………………………………………………….III

    1 Introduction ................................................................................................................... 1

    1.1 Self-assembled monolayers (SAMs) ...................................................................... 1

    1.2 Reversible self-assembled monolayers (rSAMs) .................................................... 5

    1.3 Biosensing with SAMs ........................................................................................... 8

    1.3.1 The biotin - streptavidin interaction in sensor application ............................ 12

    1.3.2 Influenza virus detection via the hemagglutinin-sialic acid interaction ........ 15

    2 Characterization Techniques ....................................................................................... 18

    2.1 Ellipsometry .......................................................................................................... 18

    2.1.1 Ellipsometry instrumentation ........................................................................ 21

    2.2 Infrared reflection adsorption spectroscopy (IRRAS) .......................................... 22

    2.3 Contact angle investigation ................................................................................... 24

    2.4 Atomic force microscopy (AFM) ......................................................................... 25

    3 Results and Discussion ................................................................................................ 26

    3.1 Synthesis of heterofunctionalized amphiphiles .................................................... 26

    3.2 Synthesis of ω-functionalized biotinylated amphiphiles ...................................... 27

    3.2.1 In-situ ellipsometry of biotinylated amphiphiles ........................................... 29

    3.2.2 IRRAS of biotinylated amphiphiles .............................................................. 46

    3.2.3 Contact angle investigation of biotinylated amphiphiles .............................. 57

    3.2.4 AFM of biotinylated amphiphiles ................................................................. 58

    3.2.5 Conclusion biotinylated amphiphiles ............................................................ 65

    3.3 Synthesis of ω-functionalized sialic acid amphiphiles ......................................... 67

    3.3.1 In-situ ellipsometry of sialic acid terminated amphiphiles ............................ 73

    3.3.2 Contact angle investigation of sialic acid terminated amphiphiles ............... 82

    3.3.3 IRRAS of sialic acid terminated amphiphiles ............................................... 83

  • 3.4 Detection of influenza virus like particles (VLPs) with sialic acid terminated

    amphiphile SAMs ............................................................................................................ 87

    3.4.1 Conclusion sialic acid terminated SAMs ...................................................... 91

    3.4.2 Comparison of the sensor devices and Outlook ............................................ 93

    4 Experimental Section ................................................................................................... 94

    4.1 Synthesis of α,ω-hetero-functionalized amphiphiles ............................................ 94

    4.1.1 Synthesis of 4-((10-bromodecyl)oxy)benzonitrile (AT1) ............................. 94

    4.1.2 Synthesis of 2-[4-(8-Bromo-octyloxy)-phenyl]-ethanol (AT2) .................... 95

    4.1.3 Pinner-Synthesis of 4-{10-[4-(2-Hydrody-ethyl)-phenyoxy]-decyloxy}-

    benzamidine hydrochloride (AT3) .............................................................................. 96

    4.1.4 Synthesis of [(4-{10-[4-(2-Hydroxy-ethyl)-phenoxy]-decyloxy}- phenyl)-

    imino-methyl]-carbamic acid tert-butyl ester (AT4) ................................................... 97

    4.1.5 Synthesis of 5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

    2-{4-[10-(4-carbamimidoyl-phenoxy)-decyloxy]-phenyl}-ethyl ester triflouro acetic

    acid (biotinylated amphiphile) (AT5) .......................................................................... 98

    4.1.6 Synthesis of 2-(2-(2-chloroethoxy)ethoxy)acetic acid (AT6) ....................... 99

    4.1.7 Synthesis of methyl 2-(2-(2-chloroethoxy)ethoxy)acetate (AT7) ............... 100

    4.1.8 Synthesis of methyl 2-(2-(2-azidoethoxy)ethoxy)acetate (AT8)................. 101

    4.1.9 Synthesis of 2-(2-(2-azidoethoxy)ethoxy)acetic acid (AT9) ....................... 102

    4.1.10 Synthesis of 4-((10-(4-(N-(tert-butoxycarbonyl)carbamimidoyl) phenoxy)

    decyl)oxy) phenethyl 2-(2-(2-azidoethoxy)ethoxy)acetate (AT10) .......................... 103

    4.1.11 Synthesis of 4-{10-[2-(2-(2-azidoethoxy)ethoxy)acetate-phenyoxy]-

    decyloxy}-benzamidine hydrochloride (AT11) ........................................................ 104

    4.1.12 Synthesis of methyl 5-acetamido-2,4-dihydroxy-6-(1,2,3-

    trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate (AT12) ................................. 105

    4.1.13 Synthesis of 3-acetamido-4-acetoxy-6-chloro-6-

    (methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (AT13) 106

    4.1.14 Synthesis of 3-acetamido-4-acetoxy-6-(but-3-yn-1-yloxy)-6-

    (methoxycarbonyl) tetrahydro-2H-pyran-2-yl) propane-1,2,3-triyl triacetate (AT14) ...

    ..................................................................................................................... 107

  • 4.1.15 Synthesis of 5-acetamido-2-(but-3-yn-1-yloxy)-4-hydroxy-6-(1,2,3-

    trihydroxypropyl) tetrahydro-2H-pyran-2-carboxylate (AT15) ................................ 108

    4.1.16 Synthesis of 5-acetamido-2-(but-3-yn-1-yloxy)-4-hydroxy-6-(1,2,3-

    trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid (AT16) ........................... 109

    4.1.17 Synthesis of (4-((10-(4-(2-(2-(2-(2-(4-(2-((-5-acetamido-2-carboxy-4-

    hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-1,2,3-

    triazol-1-yl)ethoxy)ethoxy)acetoxy) methyl)phenoxy)decyl)oxy)- benzamidine

    hydrochloride (AT17) ................................................................................................ 110

    4.2 Sample preparation ............................................................................................. 111

    4.2.1 Preparation of gold substrates ..................................................................... 111

    4.2.2 Self-assembly solution to fabricate carboxylated surfaces .......................... 111

    4.2.3 Sample preparation for in-situ ellipsometry ................................................ 111

    4.2.4 Sample preparation for contact angle investigation / IRRAS...................... 112

    4.2.5 Sample preparation for atomic force microscopy (AFM) ........................... 112

    4.2.6 Apparatus for molecule characterization ..................................................... 113

    4.2.7 Chemicals .................................................................................................... 113

    5 Literature ................................................................................................................... 115

    6 Appendix ................................................................................................................... 127

    6.1 List of abbreviations ........................................................................................... 127

    6.2 Spectra ................................................................................................................ 130

    6.3 Pubilcations ......................................................................................................... 178

    6.4 Curriculum Vitae ................................................................................................ 179

    6.5 Erklärung ............................................................................................................ 180

    6.6 Acknowledgement .............................................................................................. 181

  • I

    Summary

    The developme

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