CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 184-190
DOI: 10.1055/a-1472-6806
Focus Issue: Peter Bäuerle 65th Birthday
Original Article

Reductive Coupling Synthesis of a Soluble Poly(9,10-anthrylene ethynylene)

Isabell Geisler
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
,
Michael Forster
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
,
Bujamin Misimi
b   Bergische Universität Wuppertal, Chair of Electronic Devices and Wuppertal Center for Smart Materials & Systems, Rainer-Gruentner-Str. 21, D-42119 Wuppertal, Germany
,
Jakob Schedlbauer 
c   Universität Regensburg, Institut für Experimentelle und Angewandte Physik, Universitätsstrasse 31, D-93053 Regensburg, Germany
,
Thomas Riedl 
b   Bergische Universität Wuppertal, Chair of Electronic Devices and Wuppertal Center for Smart Materials & Systems, Rainer-Gruentner-Str. 21, D-42119 Wuppertal, Germany
,
John M. Lupton 
c   Universität Regensburg, Institut für Experimentelle und Angewandte Physik, Universitätsstrasse 31, D-93053 Regensburg, Germany
,
Ullrich Scherf 
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
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Abstract

A fully soluble poly(9,10-anthrylene ethynylene), poly[2,6-(2-octyldecyl)-9,10-anthrylene ethynylene] PAAE, with moderate degrees of polymerization Pn of ca. 10 is generated in a reductive, dehalogenative homocoupling scheme, starting from a 2,6-dialkylated 9,10-bis(dibromomethylene)-9,10-dihydroanthracene monomer and n-BuLi/CuCN as the reducing agent. PAAE shows surprisingly broad and unstructured absorption and photoluminescence emission bands with peaks at 506 nm and 611 nm, respectively, both in chloroform solution. The long absorption tail ranging into the 600–700 nm region and the large Stokes shift points to a high degree of geometrical disorder in the arrangement of the 9,10-anthrylene chromophores along the distorted polymer backbone. This disorder is borne out in the unusually strong wavelength dependence of fluorescence depolarisation, both with regards to the excitation and the emission wavelengths. Picosecond fluorescence depolarisation spectroscopy provides clear evidence for the presence of orthogonal transition dipole moments, presumably arising from the off-axis transition of the anthracene unit and the on-axis transition of the polymer backbone. Intramolecular energy relaxation then gives rise to the observed fluorescence depolarization dynamics.

Key words

conjugated polymers - poly(arylene ethynylene)s - reductive coupling - fluorescence anisotropy

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/a-1472-6806.


Dedicated to Professor Peter Bäuerle on the occasion of his 65th birthday.


Supporting Information



Publication History

Received: 13 January 2021

Accepted: 17 March 2021

Accepted Manuscript online:
01 April 2021

Article published online:
28 June 2021

© 2021. 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

  • 1 Kim M, Ryu SU, Park SA, Choi K, Kim T, Chung D, Park T. Adv. Funct. Mater. 2019; 10: 1904545
    PubMed
  • 2 So F, Krummacher B, Mathai MK, Poplavskyy D, Choulis SA, Choong V.-E. J. Appl. Phys. 2007; 102: 91101
    CrossrefPubMed
  • 3 Ragni R, Operamolla A, Farinola GM. Synthesis of Electroluminescent Conjugated Polymers for OLEDs. In Organic Light-Emitting Diodes (OLEDs) . Buckley A.. Ed.; Cambridge UK: Elsevier; 2013: 3-48
    CrossrefGoogle Scholar
  • 4 Burroughes JH, Bradley DD. C, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB. Nature 1990; 347: 539
    CrossrefPubMed
  • 5 Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
    CrossrefPubMed
  • 6 Zhou H, Chua MH, Tang BZ, Xu J. Polym. Chem. 2019; 10: 3822
    CrossrefPubMed
  • 7 Wang Y, Feng L, Wang S. Adv. Funct. Mater. 2019; 29: 1806818
    CrossrefPubMed
  • 8 Baek P, Voorhaar L, Barker D, Travas-Sejdic J. Acc. Chem. Res. 2018; 51: 1581
    CrossrefPubMed
  • 9 Yang C, Jacob J, Müllen K. Macromol. Chem. Phys. 2006; 207: 1107
    CrossrefPubMed
  • 10 Bunz UH. F. Macromol. Rapid Commun. 2009; 30: 772
    CrossrefPubMed
  • 11 Jiang D.-L, Choi C.-K, Honda K, Li W.-S, Yuzawa T, Aida T. J. Am. Chem. Soc. 2004; 126: 12084
    CrossrefPubMed
  • 12 Lee K, Cho JC, Deheck J, Kim J. Chem. Commun. 2006; 18: 1983
    CrossrefPubMed
  • 13 Zhao X, Pinto MR, Hardison LM, Mwaura J, Müller J, Jiang H, Witker D, Kleiman VD, Reynolds JR, Schanze KS. Macromolecules 2006; 39: 6355
    CrossrefPubMed
  • 14 Bunz UH. F. Chem. Rev. 2000; 100: 1605
    CrossrefPubMed
  • 15 Tarkuç S, Eelkema R, Grozema FC. Tetrahedron 2017; 73: 4994
    CrossrefPubMed
  • 16 Parada GA, Goldsmith ZK, Kolmar S, Pettersson Rimgard B, Mercado BQ, Hammarström L, Hammes-Schiffer S, Mayer JM. Science 2019; 364: 471
    CrossrefPubMed
  • 17 Eaton DF. Pure Appl. Chem. 1988; 60: 1107
    CrossrefPubMed
  • 18 Vorona MY, Yutronkie NJ, Melville OA, Daszczynski AJ, Agyei KT, Ovens JS, Brusso JL, Lessard BH. Materials 2019; 12: 2726
    CrossrefPubMed
  • 19 Wen H.-Y, Huang T.-S, Zhang H.-D, Chang M.-Y, Huang W.-Y. ACS Appl. Polym. Mater. 2019; 1: 3343
    CrossrefPubMed
  • 20 Haldar S, Chakraborty D, Roy B, Banappanavar G, Rinku K, Mullangi D, Hazra P, Kabra D, Vaidhyanathan R. J. Am. Chem. Soc. 2018; 140: 13367
    CrossrefPubMed
  • 21 Shih H.-M, Lin C.-J, Tseng S.-R, Lin C.-H, Hsu C.-S. Macromol. Chem. Phys. 2011; 212: 1100
    CrossrefPubMed
  • 22 Tember TM, Cherkasov AS. Theor. Exp. Chem. 1973; 7: 332
    CrossrefPubMed
  • 23 Sánchez-Grande A, de La Torre B, Santos J, Cirera B, Lauwaet K, Chutora T, Edalatmanesh S, Mutombo P, Rosen J, Zbořil R, Miranda R, Bjork J, Jelinek P, Martin N, Ecija D. Angew. Chem. Int. Ed. 2019; 58: 6559
    CrossrefPubMed
  • 24 Ganguly SC, Choudhury NK. Z. Phys. 1953; 135: 255
    CrossrefPubMed
  • 25 Lakowicz JR. Principles of Fluorescence Spectroscopy. Springer; Boston: 2006
    CrossrefGoogle Scholar
  • 26 Uejima M, Sato T, Tanaka K, Kaji H. Chem. Phys. 2014; 430: 47
    CrossrefPubMed
  • 27 Choudhury NK. Z. Phys. 1958; 151: 93
    CrossrefPubMed
  • 28 Men J, Ting H, Li Y, Wang W, Gao G, Xiao L, Chen Z, Wang S, Gong Q. Chem. Phys. Lett. 2014; 609: 33
    CrossrefPubMed
  • 29 Senes A, Meskers SC. J, Dijkstra WM, van Franeker JJ, Altazin S, Wilson JS, Janssen RA. J. J. Mater. Chem. C 2016; 4: 6302
    CrossrefPubMed
  • 30 Frischeisen J, Yokoyama D, Endo A, Adachi C, Brütting W. Org. Electron. 2011; 12: 809
    CrossrefPubMed
  • 31 Miteva T, Meisel A, Grell M, Nothofer HG, Lupo D, Yasuda A, Knoll W, Kloppenburg L, Bunz UH. F, Scherf U, Neher D. Synth. Met. 2000; 111-112: 173
    CrossrefPubMed
  • 32 Geisler IS. Dissertation. Bergische Universität Wuppertal; Germany: 2020
    Google Scholar
  • 33 Seidel N, Hahn T, Liebing S, Seichter W, Kortus J, Weber E. New J. Chem. 2013; 37: 601
    CrossrefPubMed
  • 34 Pola S, Kuo C.-H, Peng W.-T, Islam MM, Chao I, Tao Y.-T. Chem. Mater. 2012; 24: 2566
    CrossrefPubMed
  • 35 Baysec S, Preis E, Allard S, Scherf U. Macromol. Rapid Commun. 2016; 37: 1802
    CrossrefPubMed
  • 36 Hörhold H.-H, Gottschaldt J, Opfermann J. J. Prakt. Chem. 1977; 319: 611
    CrossrefPubMed
  • 37 Reisch H, Wiesler U, Scherf U, Tuytuylkov N. Macromolecules 1996; 29: 8204
    CrossrefPubMed
  • 38 Buckles RE, Matlack GM. Org. Synth., Coll. 1963; 4: 914 ; Org. Synth. 1951, 31, 104.
    PubMed
  • 39 Rawson RJ, Harrison IT. J. Org. Chem. 1970; 35: 2057
    CrossrefPubMed
  • 40 Iyoda M, Otani H, Oda M. Angew. Chem. 1988; 100: 1131
    CrossrefPubMed
  • 41 Nishioka T, Kuroda K, Akita M, Yoshizawa M. Angew. Chem. Int. Ed. Engl. 2019; 58: 6579
    CrossrefPubMed
  • 42 Dell'Aquila A, Marinelli F, Tey J, Keg P, Lam Y.-M, Kapitanchuk OL, Mastrorilli P, Nobile CF, Cosma P, Marchenko A, Fichou D, Mhaisalkar SG, Suranna GP, Torsi L. J. Mater. Chem. 2008; 18: 786
    CrossrefPubMed
  • 43 Keg P, Dell'Aquila A, Marinelli F, Kapitanchuk OL, Fichou D, Mastrorilli P, Romanazzi G, Suranna GP, Torsi L, Lam Y.-M, Mhaisalkar SG. J. Mater. Chem. 2010; 20: 2448
    CrossrefPubMed
  • 44 Souharce B. Dissertation. Bergische Universität Wuppertal; Germany: 2008
    Google Scholar
  • 45 Thiessen A, Würsch D, Jester SS, Aggarwal AV, Idelson A, Bange S, Vogelsang J, Höger S, Lupton JM. J. Phys. Chem. B 2015; 119: 9949
    CrossrefPubMed
  • 46 Ruseckas A, Wood P, Samuel ID. W, Webster GR, Mitchell WJ, Burn PL, Sundström V. Phys. Rev. B: Condens. Matter 2005; 72: 115214
    CrossrefPubMed