Multi-responsive Electropolymer Surface Coatings Based on Azo Molecular Switches and Carbazoles: Light, pH, and Electrochemical Control of Z→E Isomerization in Thin Films.
azobenzene
electropolymerization
molecular switches
polymer films
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Nov 2023
13 Nov 2023
Historique:
received:
11
07
2023
medline:
11
8
2023
pubmed:
11
8
2023
entrez:
11
8
2023
Statut:
ppublish
Résumé
Light-responsive surfaces are attracting increasing interest, not least because their physicochemical properties can be selectively and temporally controlled by a non-invasive stimulus. Most existing immobilization strategies involve the chemical attachment of light-responsive moieties to the surface, although this approach often suffers from a low surface concentration of active species or a high inhomogeneity of applied coatings. Herein, electropolymerization of carbazoles as a facile and rapid approach for preparing light-responsive azo-based surface coatings is presented. The electrochemical oxidative polymerization of bis-carbazole containing azo-monomers yields stable films, in which the photochemical properties and specific pH sensitivity of azo molecular switches are retained. Moreover, the molecular design enables electrocatalytic control over Z→E azo double bond isomerization facilitated by the conductive polycarbazole backbone. Ultimately, the high degree of control over macromolecular properties yields conductive surface coatings responsive to a range of stimuli, showing great promise as a strategy for versatile application in organic electronics.
Identifiants
pubmed: 37565655
doi: 10.1002/chem.202302215
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302215Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB 858
Organisme : Alexander von Humboldt-Stiftung
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
C. Buten, L. Kortekaas, B. J. Ravoo, Adv. Mater. 2020, 32, e1904957.
F. Guo, Z. Guo, RSC Adv. 2016, 6, 36623.
M. Liu, L. Jiang, Adv. Funct. Mater. 2010, 20, 3753.
X. Zhang, L. Chen, K. H. Lim, S. Gonuguntla, K. W. Lim, D. Pranantyo, W. P. Yong, W. J. T. Yam, Z. Low, W. J. Teo, H. P. Nien, Q. W. Loh, S. Soh, Adv. Mater. 2019, 31, e1804540.
T. Li, Y. Li, T. Zhang, Acc. Chem. Res. 2019, 52, 288.
P. M. Mendes, Chem. Soc. Rev. 2008, 37, 2512.
J. P. Giraldo, H. Wu, G. M. Newkirk, S. Kruss, Nat. Nanotechnol. 2019, 14, 541.
Z. L. Pianowski, Chem. Eur. J. 2019, 25, 5128.
M. Wang, Y. Yin, J. Am. Chem. Soc. 2016, 138, 6315.
X. Yu, Z. Wang, Y. Jiang, F. Shi, X. Zhang, Adv. Mater. 2005, 17, 1289.
M. Gallei, C. Rüttiger, Chem. Eur. J. 2018.
P. Brown, C. P. Butts, J. Eastoe, Soft Matter 2013, 9, 2365.
P. Uhlmann, L. Ionov, N. Houbenov, M. Nitschke, K. Grundke, M. Motornov, S. Minko, M. Stamm, Prog. Org. Coat. 2006, 55, 168.
J.-K. Chen, C.-J. Chang, Materials 2014, 7, 805.
S. Crespi, N. A. Simeth, B. König, Nat. Chem. Rev. 2019, 3, 133.
L. Kortekaas, W. R. Browne, Chem. Soc. Rev. 2019, 48, 3406.
M. Irie, T. Fukaminato, K. Matsuda, S. Kobatake, Chem. Rev. 2014, 114, 12174.
S. K. Yesodha, C. K. Sadashiva Pillai, N. Tsutsumi, Prog. Polym. Sci. 2004, 29, 45;
C. J. Barrett, J.-I. Mamiya, K. G. Yager, T. Ikeda, Soft Matter 2007, 3, 1249.
S. Kim, T. Ogata, S. Kurihara, Polym. J. 2017, 49, 407.
S. Lee, H. S. Kang, J.-K. Park, Adv. Mater. 2012, 24, 2069;
S. Santer, J. Phys. D 2018, 51, 13002.
D. Bléger, J. Schwarz, A. M. Brouwer, S. Hecht, J. Am. Chem. Soc. 2012, 134, 20597.
C. E. Weston, R. D. Richardson, P. R. Haycock, A. J. P. White, M. J. Fuchter, J. Am. Chem. Soc. 2014, 136, 11878;
L. Stricker, E.-C. Fritz, M. Peterlechner, N. L. Doltsinis, B. J. Ravoo, J. Am. Chem. Soc. 2016, 138, 4547;
L. Stricker, M. Böckmann, T. M. Kirse, N. L. Doltsinis, B. J. Ravoo, Chem. Eur. J. 2018, 24, 8639;
A. Mukherjee, M. D. Seyfried, B. J. Ravoo, Angew. Chem. Int. Ed. 2023, 25, e20230443.
P. Kumar, A. Srivastava, C. Sah, S. Devi, S. Venkataramani, Chem. Eur. J. 2019, 25, 11924.
L. Kortekaas, J. Simke, D. W. Kurka, B. J. Ravoo, ACS Appl. Mater. Interfaces 2020, 12, 32054.
L. M. Siewierski, W. J. Brittain, S. Petrash, M. D. Foster, Langmuir 1996, 12, 5838;
W. Jiang, G. Wang, Y. He, X. Wang, Y. An, Y. Song, L. Jiang, Chem. Commun. 2005, 3550.
D. T. Nguyen, M. Freitag, C. Gutheil, K. Sotthewes, B. J. Tyler, M. Böckmann, M. Das, F. Schlüter, N. L. Doltsinis, H. F. Arlinghaus, B. J. Ravoo, F. Glorius, Angew. Chem. Int. Ed. 2020, 59, 13651.
O. Roling, L. Stricker, J. Voskuhl, S. Lamping, B. J. Ravoo, Chem. Commun. 2016, 52, 1964.
S. Ludwanowski, M. Ari, K. Parison, S. Kalthoum, P. Straub, N. Pompe, S. Weber, M. Walter, A. Walther, Chem. Eur. J. 2020, 26, 13203.
R. S. L. Gibson, J. Calbo, M. J. Fuchter, ChemPhotoChem 2019, 3, 372.
J. Berson, M. Moosmann, S. Walheim, T. Schimmel, Nano Lett. 2019, 19, 816.
A. Goulet-Hanssens, M. Utecht, D. Mutruc, E. Titov, J. Schwarz, L. Grubert, D. Bléger, P. Saalfrank, S. Hecht, J. Am. Chem. Soc. 2017, 139, 335.
A. Goulet-Hanssens, C. Rietze, E. Titov, L. Abdullahu, L. Grubert, P. Saalfrank, S. Hecht, Chem 2018, 4, 1740.
A. Kravchenko, A. Shevchenko, V. Ovchinnikov, A. Priimagi, M. Kaivola, Adv. Mater. 2011, 23, 4174;
M. Otaki, R. Kumai, H. Goto, J. Polym. Sci. Polym. Chem. Ed. 2019, 57, 1756;
A. F. M. EL-Mahdy, F.-W. Lin, W.-H. Su, T. Chen, S.-W. Kuo, ACS Appl. Polym. Mater. 2020, 2, 791.
J. Tian, Z. Liu, W. Jiang, D. Shi, L. Chen, X. Zhang, G. Zhang, C. Di, D. Zhang, Angew. Chem. 2020, 132, 13948.
D. DeLongchamp, P. T. Hammond, Adv. Mater. 2001, 13, 1455.
A. Goulet-Hanssens, K. Lai Wing Sun, T. E. Kennedy, C. J. Barrett, Biomacromolecules 2012, 13, 2958.
M. Buhl, M. Tesch, S. Lamping, J. Moratz, A. Studer, B. J. Ravoo, Chem. Eur. J. 2017, 23, 6042.
S. Lamping, L. Stricker, B. J. Ravoo, Polym. Chem. 2019, 10, 683.
S. Samanta, J. Locklin, Langmuir 2008, 24, 9558;
N. B. Arndt, T. Adolphs, H. F. Arlinghaus, B. Heidrich, B. J. Ravoo, Langmuir 2023, 39, 5342.
J. Li, A. C. Grimsdale, Chem. Soc. Rev. 2010, 39, 2399;
D. Gendron, M. Leclerc, Energy Environ. Sci. 2011, 4, 1225.
M. Ates, Mater. Sci. Eng. C 2013, 33, 1853.
M. Zhao, H. Zhang, C. Gu, Y. Ma, J. Mater. Chem. C 2020, 8, 5310.
H. Wang, J. Lin, Z. X. Shen, J. Sci. Adv. Mater. Devices 2016, 1, 225.
R. J. Waltman, J. Bargon, Can. J. Chem. 1986, 64, 76.
R. Zhao, X. Zhan, L. Yao, Q. Chen, Z. Xie, Y. Ma, Macromol. Rapid Commun. 2016, 37, 610.
D. Yiğit, S. O. Hacioglu, M. Güllü, L. Toppare, Electrochim. Acta 2016, 196, 140.
H. Logtenberg, W. R. Browne, Org. Biomol. Chem. 2013, 11, 233.
K. Wagner, R. Byrne, M. Zanoni, S. Gambhir, L. Dennany, R. Breukers, M. Higgins, P. Wagner, D. Diamond, G. G. Wallace, D. L. Officer, J. Am. Chem. Soc. 2011, 133, 5453.
L. Kortekaas, O. Vlasenko, J. T. van Herpt, W. R. Browne, J. Am. Chem. Soc. 2016, 138, 1301.
M. T. W. Milder, J. L. Herek, J. Areephong, B. L. Feringa, W. R. Browne, J. Phys. Chem. A 2009, 113, 7717;
M. Gicevicius, G. Bagdziunas, Y. Abduloglu, A. Ramanaviciene, O. Gumusay, M. Ak, T. Soganci, A. Ramanavicius, ChemPhysChem 2018, 19, 2735.
A. Gibalova, N. B. Arndt, L. Burg, B. J. Ravoo, ACS Appl. Mater. Interfaces 2023, 15, 12363.
L. Kortekaas, J. Simke, N. B. Arndt, M. Böckmann, N. L. Doltsinis, B. J. Ravoo, Chem. Sci. 2021, 12, 11338;
J. Rickhoff, N. B. Arndt, M. Böckmann, N. L. Doltsinis, B. J. Ravoo, L. Kortekaas, J. Org. Chem. 2022, 87, 10605.
E. J. Gonzalez Lopez, M. Renfige Rodriguez, S. C. Santamarina, L. Macor, L. A. Otero, M. A. Gervaldo, A. M. Durantini, E. N. Durantini, J. E. Durantini, D. A. Heredia, ACS Appl. Polym. Mater. 2023, 5, 943.
L. Lee, Y. R. Leroux, P. Hapiot, A. J. Downard, Langmuir 2015, 31, 5071.
N. Elgrishi, K. J. Rountree, B. D. McCarthy, E. S. Rountree, T. T. Eisenhart, J. L. Dempsey, J. Chem. Educ. 2018, 95, 197.
A. I. Hanopolskyi, S. De, M. J. Białek, Y. Diskin-Posner, L. Avram, M. Feller, R. Klajn, J. Org. Chem. 2019, 15, 2398.
Y. Gong, Y. Guo, F. Ge, W. Xiong, J. Su, Y. Sun, C. Zhang, A.-M. Cao, Y. Zhang, J. Zhao, Y. Che, Angew. Chem. Int. Ed. 2020, 59, 10337.
Q. Chen, D.-P. Liu, J.-H. Zhu, B.-H. Han, Macromolecules 2014, 47, 5926.