Subscribe to RSS
DOI: 10.1055/a-1472-6806
Reductive Coupling Synthesis of a Soluble Poly(9,10-anthrylene ethynylene)
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 anisotropySupporting 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.
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/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Kim M, Ryu SU, Park SA, Choi K, Kim T, Chung D, Park T. Adv. Funct. Mater. 2019; 10: 1904545
- 2 So F, Krummacher B, Mathai MK, Poplavskyy D, Choulis SA, Choong V.-E. J. Appl. Phys. 2007; 102: 91101
- 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
- 4 Burroughes JH, Bradley DD. C, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB. Nature 1990; 347: 539
- 5 Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
- 6 Zhou H, Chua MH, Tang BZ, Xu J. Polym. Chem. 2019; 10: 3822
- 7 Wang Y, Feng L, Wang S. Adv. Funct. Mater. 2019; 29: 1806818
- 8 Baek P, Voorhaar L, Barker D, Travas-Sejdic J. Acc. Chem. Res. 2018; 51: 1581
- 9 Yang C, Jacob J, Müllen K. Macromol. Chem. Phys. 2006; 207: 1107
- 10 Bunz UH. F. Macromol. Rapid Commun. 2009; 30: 772
- 11 Jiang D.-L, Choi C.-K, Honda K, Li W.-S, Yuzawa T, Aida T. J. Am. Chem. Soc. 2004; 126: 12084
- 12 Lee K, Cho JC, Deheck J, Kim J. Chem. Commun. 2006; 18: 1983
- 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
- 14 Bunz UH. F. Chem. Rev. 2000; 100: 1605
- 15 Tarkuç S, Eelkema R, Grozema FC. Tetrahedron 2017; 73: 4994
- 16 Parada GA, Goldsmith ZK, Kolmar S, Pettersson Rimgard B, Mercado BQ, Hammarström L, Hammes-Schiffer S, Mayer JM. Science 2019; 364: 471
- 17 Eaton DF. Pure Appl. Chem. 1988; 60: 1107
- 18 Vorona MY, Yutronkie NJ, Melville OA, Daszczynski AJ, Agyei KT, Ovens JS, Brusso JL, Lessard BH. Materials 2019; 12: 2726
- 19 Wen H.-Y, Huang T.-S, Zhang H.-D, Chang M.-Y, Huang W.-Y. ACS Appl. Polym. Mater. 2019; 1: 3343
- 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
- 21 Shih H.-M, Lin C.-J, Tseng S.-R, Lin C.-H, Hsu C.-S. Macromol. Chem. Phys. 2011; 212: 1100
- 22 Tember TM, Cherkasov AS. Theor. Exp. Chem. 1973; 7: 332
- 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
- 24 Ganguly SC, Choudhury NK. Z. Phys. 1953; 135: 255
- 25 Lakowicz JR. Principles of Fluorescence Spectroscopy. Springer; Boston: 2006
- 26 Uejima M, Sato T, Tanaka K, Kaji H. Chem. Phys. 2014; 430: 47
- 27 Choudhury NK. Z. Phys. 1958; 151: 93
- 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
- 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
- 30 Frischeisen J, Yokoyama D, Endo A, Adachi C, Brütting W. Org. Electron. 2011; 12: 809
- 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
- 32 Geisler IS. Dissertation. Bergische Universität Wuppertal; Germany: 2020
- 33 Seidel N, Hahn T, Liebing S, Seichter W, Kortus J, Weber E. New J. Chem. 2013; 37: 601
- 34 Pola S, Kuo C.-H, Peng W.-T, Islam MM, Chao I, Tao Y.-T. Chem. Mater. 2012; 24: 2566
- 35 Baysec S, Preis E, Allard S, Scherf U. Macromol. Rapid Commun. 2016; 37: 1802
- 36 Hörhold H.-H, Gottschaldt J, Opfermann J. J. Prakt. Chem. 1977; 319: 611
- 37 Reisch H, Wiesler U, Scherf U, Tuytuylkov N. Macromolecules 1996; 29: 8204
- 38 Buckles RE, Matlack GM. Org. Synth., Coll. 1963; 4: 914 ; Org. Synth. 1951, 31, 104.
- 39 Rawson RJ, Harrison IT. J. Org. Chem. 1970; 35: 2057
- 40 Iyoda M, Otani H, Oda M. Angew. Chem. 1988; 100: 1131
- 41 Nishioka T, Kuroda K, Akita M, Yoshizawa M. Angew. Chem. Int. Ed. Engl. 2019; 58: 6579
- 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
- 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
- 44 Souharce B. Dissertation. Bergische Universität Wuppertal; Germany: 2008
- 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
- 46 Ruseckas A, Wood P, Samuel ID. W, Webster GR, Mitchell WJ, Burn PL, Sundström V. Phys. Rev. B: Condens. Matter 2005; 72: 115214