Skip to main content
SpringerLink
Log in

Diazene sulphonate as a cross-linking agent for polymers with pendant triarylamine hole-conducting units

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Diazene sulphonates are readily available compounds which are soluble in water and polar solvents. They strongly absorb the UV-VIS light and they decompose under UV irradiation via radical or ionic intermediates. These properties render them valuable, e.g. for analytical purposes and for photo-printing. In this presentation, it will be demonstrated that polymers with a pendant diazene sulphonate function as cross-linking agents and with pendant aromatic amines as hole-transporters can be considered as useful materials for organic light-emitting device (OLED) technology.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Bamberger, E. (1894). Ueber Stereomerie bei Diazoverbindungen und die Natur der Isodiazokorper. Berichte der deutschen chemischen Gesellschaft, 27, 2582–2595. DOI: 10.1002/cber.189402702264. (in German)

    Article  Google Scholar 

  • Dauth, J. (1991). Neue Azo-, Triazen- und Peroxyverbindungen im Thermo- und Photodruck. Ph.D. thesis, University of Bayreuth, Germany. (in German)

    Google Scholar 

  • Dauth, J., Nuyken, O., Strohriegl, P., & Voit, B. (1992). Watersoluble photoresins based on azosulfonates. Die Makromolekulare Chemie, 193, 723–734. DOI: 10.1002/macp.1992. 021930318.

    Article  CAS  Google Scholar 

  • de Jonge, J., & Dijkstra, R. (1956). Some photochemical properties of alkali salts of aryldiazosulphonic acids. Recueil des Travaux Chimiques des Pays-Bas, 75, 290–300. DOI: 10.1002/recl. 19560750308.

    Article  Google Scholar 

  • Dunkin, I. R., Gittinger, A., Sherrington, D. C., & Whittaker, P. (1996). Synthesis, characterization and applications of azo-containing photodestructible surfactants. Journal of the Chemical Society, Perkin Transactions, 2, 1996, 1837–1842. DOI: 10.1039/p29960001837.

    Article  Google Scholar 

  • Eastoe, J. (2006). Photo-destructible surfactants in microemulsions. In W. Richtering (Ed.), Smart colloidal materials (Series: Progress in colloid and polymer science, Vol. 133, pp. 106–110). Berlin, Germany: Springer. DOI: 10.1007/3-54032702-9-17.

    Article  CAS  Google Scholar 

  • Faber, R., Mielke, G. F., Rapta, P., Stasko, A., & Nuyken, O. (2000). Anodic oxidation of novel hole-transporting materials derived from tetraarylbenzidines. Electrochemical and spectroscopic characterization. Collection of Czechoslovak Chemical Communications, 65, 1403–1418. DOI: 10.1135/cccc20001403.

    Article  CAS  Google Scholar 

  • Faber, R. (2001). Neue Polymere fur organische LEDs auf der Basis von Fluorenylidenverknüpften Oligo(p-phenylen)en. Ph.D. thesis, Technical University of Munich, Germany. (in German)

    Google Scholar 

  • Franzke, D., Voit, B., Nuyken, O., & Wokaun, A. (1992a). Wavelength-dependent photolysis of 3-vinyl-phenyl-azosul-fonate. Journal of Photochemistry and Photobiology A: Chemistry, 68, 205–212. DOI: 10.1016/1010-6030(92)85184-v.

    Article  CAS  Google Scholar 

  • Franzke, D., Voit, B., Nuyken, O., & Wokaun, A. (1992b). Pulsed ultraviolet laser photolysis of substituted phenyl azo-sulfonates: Wavelength dependent effects. Molecular Physics, 77, 397–409. DOI: 10.1080/00268979200102511.

    Article  CAS  Google Scholar 

  • Freeman, H. C., & Le Fevre, R. J. W. (1951). Hantzsch’s isomeric diazosulphonates. Journal of the Chemical Society, 1951, 415–428. DOI: 10.1039/jr9510000415.

    Article  Google Scholar 

  • Geckeler, K. E., Nuyken, O., Schnoller, U., Thünemann, A., & Voit, B. (2000). Complexing behavior of diazosulfonate polymer. In Y. Yagci, M. K. Mishra, O. Nuyken, K. Ito, & K. Wnek (Eds.), Tailored polymers & applications (pp. 287–296). Leiden, the Netherlands: VSP International Publishers.

    Google Scholar 

  • Georgi, U. (2014). Synthese photoaktiver Polymere zur optischen Strukturierung dunner Schichten. Ph.D. thesis, Dresden University of Technology, Germany. (in German)

    Google Scholar 

  • Girad, E. (1972). FR Patent No. 2090801. Paris, France: INPI.

    Google Scholar 

  • Hantzsch, A. (1894). Ueber Stereoisomerie bei Diazoverbindungen und die Natur der Isodiazokoürper. Berichte der deutschen chemischen Gesellschaft, 27, 1702–1725. DOI: 10.1002/cber.189402702110. (in German)

    Article  Google Scholar 

  • Hantzsch, A., & Borghaus, H. (1897). Ueber Bis-Diazoniumsalze. Berichte der deutschen chemischen Gesellschaft, 30, 9293. DOI: 10.1002/cber.18970300115. (in German)

    Google Scholar 

  • Hodgson, H. H., & Marsden, E. (1943). The decomposition of diazo-compounds in neutral solution. Some observations on the diazo-coupling reaction. Journal of the Chemical Society, 1943, 379–380. DOI: 10.1039/jr9430000379.

    Article  Google Scholar 

  • Jonker, H., Thijssens, T. P. G. W., & van Beek, L. K. H. (1968). Properties of diazosulfonates. Part VI: Quantum yields for the photolysis of 2-methoxybenzenediazonium and for the photo-isomerization of 2-methoxybenzene-trans-diazosulfonate. Recueil des Travaux Chimiques des Pays-Bas, 87, 997–1005. DOI: 10.1002/recl.19680870903.

    Article  CAS  Google Scholar 

  • Kerber, R., Nuyken, O., & Dorn, M. (1978). “Über die Copolymerization von (3-vinylphenylazo)-methylmalonodinitril mit Styrol 7. Mitteilung uüber Azoinitiatoren. Die Makromolekulare Chemie, 179, 1803–1814. DOI: 10.1002/macp.1978.0217 90715.

    Article  CAS  Google Scholar 

  • Knepper, T. (1987). Synthese unsymmetrischer Azoverbindungen und ihr Verhalten bei Photoreaktionen. Diploma thesis, University of Mainz, Germany. (in German)

    Google Scholar 

  • Lewis, E. S., & Suhr, H. (1959). Untersuchungen über die Reaktion von Diazoniumsalzen mit Sulfit. Chemische Berichte, 92, 3031–3043. DOI: 10.1002/cber.19590921205. (in German)

    Article  CAS  Google Scholar 

  • Lichnerova, E. (2005). Neue vernetzbare Polymere fur die OLED-Technologie. Ph.D. thesis, Technical University of Munich, Germany. (in German)

    Google Scholar 

  • Liu, S., Jiang, X., Ma, H., Liu, M. S., & Jen, A. K. Y. (2000). Triarylamine-containing poly(perfluorocyclobutane) as hole-transporting material for polymer light-emitting diodes. Macromolecules, 33, 3514–3517. DOI: 10.1021/ma0002038.

    Article  CAS  Google Scholar 

  • Ma, B., Lauterwasser, F., Deng, L., Zonte, C. S., Kim, B. J., Fréchet, J. M. J., Borek, C., & Thompson, M. E. (2007). New thermally cross-linkable polymer and its application as a hole-transporting layer for solution processed multilayer organic light emitting diodes. Chemistry of Materials, 19, 4827–4832. DOI: 10.1021/cm0715500.

    Article  CAS  Google Scholar 

  • Matusche, P. (1995). Polymere Diazosulfonate: Synthese, Eigenschaften und Anwendungen im Photodruck sowie als Nachweisreagenz fur phenolische Naturstoffe. Ph.D. thesis, Technical University of Munich, Germany. (in German)

    Google Scholar 

  • Matusche, P., Nuyken, O., Voit, B., Van Damme, M., Vermeersch, J., De Winter, W., & Alaerts, L. (1995). Water soluble photoresins based on polymeric azo compounds. Reactive Polymers, 24, 271–278. DOI: 10.1016/0923-1137(94)00093-k.

    Article  CAS  Google Scholar 

  • Matusche, P., Nuyken, O., & Voit, B. (1997a). Low-molar mass and polymeric diazosulfonates as disguised diazonium ions for application as analytical reagents in quick assays. Die Angewandte Makromolekulare Chemie, 250, 45–65. DOI: 10.1002/apmc.1997.052500104.

    Article  CAS  Google Scholar 

  • Matusche, P., Nuyken, O., Voit, B., & Van Damme, M. (1997b). Water soluble and photoactive copolymers containing amidic aryldiazosulfonate groups. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 34, 201–209. DOI: 10.1080/10601329708014947.

    Article  Google Scholar 

  • Mezger, T., Nuyken, O., Meindl, K., & Wokaun, A. (1996). Light decomposable emulsifiers: application of alkyl-substituted aromatic azosulfonates in emulsion polymerization. Progress in Organic Coatings, 29, 147–157. DOI: 10.1016/s0300-9440(96)00666-2.

    Article  CAS  Google Scholar 

  • Neta, P., & Huie, R. E. (1985). Freeradical chemistry of sulfite. Environmental Health Perspectives, 64, 209–217.

    Article  CAS  Google Scholar 

  • Nuyken, O., & Voit, B. (1989). Water-soluble and photosensitive copolymers from methyl methacrylate and sodium — vinylphenylazosulfonate. Die Makromolekulare Chemie, 190, 1325–1332. DOI: 10.1002/macp.1989.021900613.

    Article  CAS  Google Scholar 

  • Nuyken, O., Knepper, T., Voit, B., & Pask, S. D. (1991). U.S. Patent No. 5037961 (A). Washington, D.C., USA: U.S. Patent and Trademark Office.

    Google Scholar 

  • Nuyken, O., Dauth, J. W., & Vermeersch, J. T. (1992). European Patent Application No. 0507008 (A1). Munich, Germany: European Patent Office.

    Google Scholar 

  • Nuyken, O., Dauth, J., Voit, B., & Strohriegl, P. (1993). Hightech applications of polymeric azo compounds. In J. Kahovec (Ed.), Macromolecules 1992 Invited lectures of the 34th IU-PAC International Symposium on Macromolecules (pp. 119–131). Utrecht, the Netherlands: VSP.

    Google Scholar 

  • Nuyken, O., Meindl, K., Wokaun, A., & Mezger, T. (1994). Photolabile surfactants based on the diazosulfonate group I. 4-n-Alkylbenzenediazosulfonates. Journal of Photochemistry and Photobiology A: Chemistry, 81, 45–53. DOI: 10.1016/1010-6030(93)03771-8.

    Article  CAS  Google Scholar 

  • Nuyken, O., Meindl, K., Wokaun, A., & Mezger, T. (1995). Photolabile surfactants based on the diazosulphonate group 2. 4-(Acyloxy)benzenediazosulphonates and 4-(acylamino)benz-enediazosulphonates. Journal of Photochemistry and Photobiology A: Chemistry, 85, 291–298. DOI: 10.1016/1010-6030(94)03919-1.

    Article  CAS  Google Scholar 

  • Nuyken, O., & Voit, B. (1997). The photoactive diazosulfonate group and its role in polymer chemistry. Macromolecular Chemistry and Physics, 198, 2337–2372. DOI: 10.1002/macp.1997.021980801.

    Article  CAS  Google Scholar 

  • Nuyken, O., Jungermann, S., Wiederhirn, V., Bacher, E., & Meerholz, K. (2006). Modern trends in organic light-emitting devices (OLEDs). Monatshefte für Chemie, 137, 811–824. DOI: 10.1007/s00706-006-0490-4.

    Article  CAS  Google Scholar 

  • Nuyken, O. (2014). Trends in den Polymerwissenschaften. Chemie in Unserer Zeit, 48, 270–283. DOI: 10.1002/ciuz.201 400667. (in German)

    Article  CAS  Google Scholar 

  • Rapta, P., Stasko, A., Bustin, D., Nuyken, O., & Voit, B. (1992). Electrochemical reduction of azo sulfonates and sulfones. A cyclic voltammetry and EPR study. Journal of the Chemical Society, Perkin Transactions, 2, 1992, 2049–2055. DOI: 10.1039/p29920002049.

    Article  Google Scholar 

  • Reichenbach, P. (2011). Metallische Nanoantennen: Frequenzverdopplung und photochemische Reaktionen auf kleinen Skalen. Ph.D. thesis, Dresden University of Technology, Germany. (in German)

    Google Scholar 

  • Schelter, J., Mielke, G. F., Kohnen, A., Wies, J., Kober, S., Nuyken, O., & Meerholz, K. (2010). Novel non-conjugated main-chain hole-transporting polymers for organic electronics application. Macromolecular Rapid Communications, 31, 1560–1567. DOI: 10.1002/marc.201000125.

    Article  CAS  Google Scholar 

  • Schmitt, K., & Glutz, L. (1869). Ueber Diazophenole. Berichte der deutschen chemischen Gesellschaft, 2, 51–53. DOI: 10.1002/cber.18690020124. (in German)

    Article  Google Scholar 

  • Schnoller, U. (1996). Synthese und Eigenschaften neuer diazo-sulfonathaltiger Polymere fur die Anwendung im Thermo- und Photodruck und in Polyelektrolyt-Tensid-Komplexen. Ph.D. thesis, Technical University of Munich, Germany. (in German)

    Google Scholar 

  • Spiertz, E., & van Beek, L. (1974). U.S. Patent No. 3802886 (A). Washington, D.C., USA: U.S. Patent and Trademark Office.

    Google Scholar 

  • Stampor, W., & Mróz, W. (2007). Electroabsorption in triphe-nylamine-based hole-transporting materials for organic light-emitting diodes. Chemical Physics, 331, 261–269. DOI: 10.1016/j.chemphys.2006.10.014.

    Article  CAS  Google Scholar 

  • Staško, A., Szaboova, K., Cholvad, V., Nuyken, O., & Dauth, J. (1993). The photochemical decomposition of azo compounds (a spin trap study). Journal of Photochemistry and Photobiology A: Chemistry, 69, 295–304. DOI: 10.1016/1010-6030(93)85095-p.

    Article  Google Scholar 

  • Thünemann, A. F., Schnöller, U., Nuyken, O., & Voit, B. (1999). Self-assembled complexes of diazosulfonate polymers with low surface energies. Macromolecules, 32, 7414–7421. DOI: 10.1021/ma990868d.

    Article  Google Scholar 

  • Trogisch, S. (2003). Optische Strukturierung ultradünner funktioneller Polymerfilme. Ph.D. thesis, Dresden University of Technology, Germany. (in German)

    Google Scholar 

  • van Aert, H., van Damme, M., Nuyken, O., Schnoller, U., Eichhorn, K. J., Grundke, K., & Voit, B. (2001). Imagewise structuring of diazosulfonate polymer films by UV light and laser irradiation — a comparison. Macromolecular Materials and Engineering, 286, 488–496. DOI: 10.1002/1439-2054(200108)286:8< 488::AID-MAME488> 3.0.CO;2-F.

    Article  Google Scholar 

  • van Beek, L. K. H., Hellferich, J., Jonker, H., & Thijssens, T. P. G. W. (1967a). Properties of diazosulfonates. Part I: The dissociation of methoxybenzenediazosulfonates. Recueil des Travaux Chimiques des Pays-Bas, 86, 405–409. DOI: 10.1002/recl.19670860409.

    Article  Google Scholar 

  • van Beek, L. K. H., Hellferich, J., Jonker, H., & Thijssens, T. P. G. W. (1967b). Properties of diazosulfonates. Part II: The rate of the reaction between 2-methoxybenzenediazonium and sulfite ions. Recueil des Travaux Chimiques des Pays-Bas, 86, 749–754. DOI: 10.1002/recl.19670860710.

    Article  Google Scholar 

  • van der Veen, J., Helfferich, J., & van Beek, L. K. H. (1966). Photo isomerization of methoxybenzene diazosulfonates. Recueil des Travaux Chimiques des Pays-Bas, 85, 895–898. DOI: 10.1002/recl.19660850907.

    Article  Google Scholar 

  • Voit, B., Braun, F., Gernert, M., Sieczkowska, B., Millaruelo, M., Messerschmidt, M., Mertig, M., & Opitz, J. (2006). Photolabile and thermally labile polymers as templates and for surface patterning. Polymers for Advanced Technologies, 17, 691–693. DOI: 10.1002/pat.793.

    Article  CAS  Google Scholar 

  • Voit, B., Braun, F., Stadermann, J., & Riedel, M. (2010). Multifunctional polymers for micro and nano patterned thin films. Polymer Preprints, 51, 211.

    CAS  Google Scholar 

  • Wittenbeck, P., Franzke, D., & Wokaun, A. (1990). Photochemically induced breakdown of rod-like micelles: light-induced viscosity changes. Journal of Photochemistry and Photobiology A: Chemistry, 53, 343–358. DOI: 10.1016/1010-6030(90)87138-2.

    Article  CAS  Google Scholar 

  • Wolfe, J. P., & Buchwald, S. L. (1997a). Room temperature catalytic amination of aryl iodides. The Journal of Organic Chemistry, 62, 6066–6068. DOI: 10.1021/jo970876x.

    Article  CAS  Google Scholar 

  • Wolfe, J. P., & Buchwald, S. L. (1997b). Improved functional group compatibility in the palladium-catalyzed amination of aryl bromides. Tetrahedron Letters, 38, 6359–6362. DOI: 10.1016/s0040-4039(97)01463-9.

    Article  CAS  Google Scholar 

  • Yang, Z., & Cao, W. (2004). Self-assembliesof poly(4-diazonium styrene. Macromolecular Chemistry and Physics, 205, 241–246. DOI: 10.1002/macp.200300020.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biomedical Centre BioMed, Division of Neuroscience, Comenius University, Jessenins Faculty of Medicine, Mala Hora 4, 036 01, Martin, Slovakia

    Eva Baranovicova

  2. Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Andrej Stasko

  3. Wacker-Lehrstuhl für Makromolekulare Chemie, TU München, Lichtenbergstrasse 4, 85747, Garching, Germany

    Oskar Nuyken

Authors
  1. Eva Baranovicova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrej Stasko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Oskar Nuyken
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Oskar Nuyken.

Additional information

Dedicated to Prof. Dr. Robert Kerber on the occasion of his 90th birthday

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baranovicova, E., Stasko, A. & Nuyken, O. Diazene sulphonate as a cross-linking agent for polymers with pendant triarylamine hole-conducting units. Chem. Pap. 70, 1238–1252 (2016). https://doi.org/10.1515/chempap-2016-0063

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1515/chempap-2016-0063

Keywords

Search

Navigation