Calamitic Liquid Crystals for Reversible Light-Modulated Phase Regulation Based on Arylazopyrazole Photoswitches.
azoheteroarene
liquid crystals
molecular photoswitches
phase regulation
photoresponsive materials
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
09 Nov 2023
09 Nov 2023
Historique:
received:
28
10
2023
pubmed:
9
11
2023
medline:
9
11
2023
entrez:
9
11
2023
Statut:
aheadofprint
Résumé
The design of responsive liquid crystals enables a diversity of technological applications. Especially photochromic liquid crystals gained a lot of interest in recent years due to the excellent spatiotemporal control of their phase transitions. In this work we present calamitic light responsive mesogens based on a library of arylazopyrazole photoswitches. These compounds show liquid-crystalline behavior as shown by differential scanning calorimetry, grazing incidence X-ray diffraction and polarized optical microscopy. UV-vis spectroscopy and NMR analysis confirmed the excellent photophysical properties in solution and thin film. Additionally, polarized optical microscopy studies of the pristine compounds show reversible phase transition upon irradiation with light. Moreover, as a dopant in the commercially available liquid crystal 4-cyano-4'-pentylbiphenyl (5CB), the temperature range was reduced to ambient temperatures while preserving the photophysical properties. Remarkably, this co-assembled system shows reversible liquid-crystalline to isotropic phase transition upon irradiation with light of different wavelengths. The spatiotemporal control of the phase transition of the liquid crystals offers opportunities in the development of optical devices.
Identifiants
pubmed: 37944022
doi: 10.1002/chem.202302958
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302958Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : IRTG 2678
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
H. Yu, T. Ikeda, Adv. Mater. 2011, 23, 2149-2180;
E.-K. Fleischmann, R. Zentel, Angew. Chem. Int. Ed. 2013, 52, 8810-8827;
X. Wang, D. S. Miller, J. J. De Pablo, N. L. Abbott, Adv. Funct. Mater. 2014, 24, 6219-6226;
J. E. Stumpel, E. R. Gil, A. B. Spoelstra, C. W. M. Bastiaansen, D. J. Broer, A. P. H. J. Schenning, Adv. Funct. Mater. 2015, 25, 3314-3320;
E. Bukusoglu, M. Bedolla Pantoja, P. C. Mushenheim, X. Wang, N. L. Abbott, Annu. Rev. Chem. Biomol. Eng. 2016, 7, 163-196;
R. S. Zola, H. K. Bisoyi, H. Wang, A. M. Urbas, T. J. Bunning, Q. Li, Adv. Mater. 2019, 31, e1806172;
H. K. Bisoyi, Q. Li, Chem. Rev. 2022, 122, 4887-4926;
J. Gao, Y. Tang, D. Martella, J. Guo, D. S. Wiersma, Q. Li, Responsive Mater. 2023, 1.
T. Kosa, L. Sukhomlinova, L. Su, B. Taheri, T. J. White, T. J. Bunning, Nature 2012, 485, 347-349;
S. Paoloni, F. Mercuri, M. Marinelli, R. Pizzoferrato, U. Zammit, T. Kosa, L. Sukhomlinova, B. Taheri, J. Chem. Phys. 2015, 143, 134901;
J. Noga, A. Sobolewska, S. Bartkiewicz, Z. Galewski, Liq. Cryst. 2016, 43, 758-769;
M. Rumi, S. A. Cazzell, T. Kosa, L. Sukhomlinova, B. Taheri, T. J. White, T. J. Bunning, Phys. Rev. E. 2016, 93, 32701;
S. Paoloni, F. Mercuri, U. Zammit, Int. J. Thermophys. 2019, 40, 170;
H. Wang, H. K. Bisoyi, X. Zhang, F. Hassan, Q. Li, Chem. Eur. J. 2022, 28, e202103906;
W. Kang, Y. Tang, X. Meng, S. Lin, X. Zhang, J. Guo, Q. Li, Angew. Chem. Int. Ed. 2023, 62, e202311486;
H. Wang, Y. Tang, H. Krishna Bisoyi, Q. Li, Angew. Chem. Int. Ed. 2023, 135, e202216600.
T. Ikeda, J. Mater. Chem. 2003, 13, 2037-2057;
T. Ikeda, O. Tsutsumi, Science 1995, 268, 1873-1875;
S. Tazuke, S. Kurihara, T. Ikeda, Chem. Lett. 1987, 16, 911-914.
Q. Wang, H. Chen, H. Xing, Y. Deng, Z.-W. Luo, H.-L. Xie, Crystals 2021, 11, 418;
J.-H. Sung, S. Hirano, O. Tsutsumi, A. Kanazawa, T. Shiono, T. Ikeda, Chem. Mater. 2002, 14, 385-391;
C. H. Legge, G. R. Mitchell, J. Phys. D 1992, 25, 492-499;
S. Kurihara, T. Ikeda, S. Tazuke, J. Seto, J. Chem. Soc. Faraday Trans. 1991, 87, 3251-3254.
A. Sobolewska, J. Zawada, S. Bartkiewicz, Z. Galewski, J. Mater. Chem. C 2013, 117, 10051-10058;
A. Sobolewska, S. Bartkiewicz, J. Mysliwiec, K. D. Singer, J. Mater. Chem. C 2014, 2, 1409-1412;
H. K. Bisoyi, Q. Li, Chem. Rev. 2016, 116, 15089-15166;
A. Miniewicz, H. Orlikowska, A. Sobolewska, S. Bartkiewicz, Phys. Chem. Chem. Phys. 2018, 20, 2904-2913.
S. Kurihara, D. Yoneyama, T. Nonaka, Chem. Mater. 2001, 13, 2807-2812;
G. Wang, M. Zhang, T. Zhang, J. Guan, H. Yang, RSC Adv. 2012, 2, 487-493;
W.-C. Xu, S. Sun, S. Wu, Angew. Chem. Int. Ed. 2019, 58, 9712-9740;
F. Malotke, M. Spengler, L. Pschyklenk, M. Saccone, P. Kaul, M. Giese, Adv. photonics 2022, 3, 2100353.
M. Pfletscher, S. Hölscher, C. Wölper, M. Mezger, M. Giese, Chem. Mater. 2017, 29, 8462-8471;
M. Pfletscher, C. Wölper, J. S. Gutmann, M. Mezger, M. Giese, Chem. Commun. 2016, 52, 8549-8552;
S. Pan, M. Ni, B. Mu, Q. Li, X.-Y. Hu, C. Lin, D. Chen, L. Wang, Adv. Funct. Mater. 2015, 25, 3571-3580;
K. Kreger, P. Wolfer, H. Audorff, L. Kador, N. Stingelin-Stutzmann, P. Smith, H.-W. Schmidt, J. Am. Chem. Soc. 2010, 132, 509-516.
Z.-W. Luo, L. Tao, C.-L. Zhong, Z.-X. Li, K. Lan, Y. Feng, P. Wang, H.-L. Xie, Macromolecules 2020, 53, 9758-9768;
P. Zhang, A. J. J. Kragt, A. P. H. J. Schenning, L. T. de Haan, G. Zhou, J. Mater. Chem. C 2018, 6, 7184-7187;
S. V. Serak, N. V. Tabiryan, G. Assanto, Mol. Cryst. 2012, 559, 202-213;
Q. Zhang, K. Wang, Q. Ren, Li Niu, B. Chen, Liq. Cryst. 2011, 38, 1349-1355;
K. Ichimura, Chem. Rev. 2000, 100, 1847-1874.
A. Mukherjee, M. D. Seyfried, B. J. Ravoo, Angew. Chem. Int. Ed. 2023;
A. Gibalova, N. B. Arndt, L. Burg, B. J. Ravoo, ACS Appl. Mater. Interfaces. 2023, 15, 12363-12371;
N. B. Arndt, T. Adolphs, H. F. Arlinghaus, B. Heidrich, B. J. Ravoo, Langmuir 2023, 39, 5342-5351;
N. B. Arndt, F. Schlüter, M. Böckmann, T. Adolphs, H. F. Arlinghaus, N. L. Doltsinis, B. J. Ravoo, Langmuir 2022, 38, 735-742;
S. Crespi, N. A. Simeth, B. König, Nat. Chem. Rev. 2019, 3, 133-146;
L. Stricker, M. Böckmann, T. M. Kirse, N. L. Doltsinis, B. J. Ravoo, Chem. Eur. J. 2018, 24, 8639-8647;
J. Calbo, C. E. Weston, A. J. P. White, H. S. Rzepa, J. Contreras-García, M. J. Fuchter, J. Am. Chem. Soc. 2017, 139, 1261-1274;
L. Stricker, E.-C. Fritz, M. Peterlechner, N. L. Doltsinis, B. J. Ravoo, J. Am. Chem. Soc. 2016, 138, 4547-4554;
C. E. Weston, R. D. Richardson, P. R. Haycock, A. J. P. White, M. J. Fuchter, J. Am. Chem. Soc. 2014, 136, 11878-11881.
S. Devi, M. Saraswat, S. Grewal, S. Venkataramani, J. Org. Chem. 2018, 83, 4307-4322;
Y.-T. Wang, X.-Y. Liu, G. Cui, W.-H. Fang, W. Thiel, Angew. Chem. Int. Ed. 2016, 55, 14009-14013.
P. Kumar, I. Bala, R. De, S. Kumar Pal, S. Venkataramani, Chem. Eur. J. 2022, 29, e202202876.
V. Adam, D. K. Prusty, M. Centola, M. Škugor, J. S. Hannam, J. Valero, B. Klöckner, M. Famulok, Chem. Eur. J. 2018, 24, 1062-1066.
C. T. Imrie, L. Taylor, Liq. Cryst. 1989, 6, 1-10;
H. A. Ahmed, M. Hagar, G. R. Saad, Liq. Cryst. 2019, 46, 1611-1620.
Y. Zhou, K. Jie, F. Huang, Org. Chem. Front. 2017, 4, 2387-2391.
M. Pfletscher, M. Mezger, M. Giese, Soft Matter 2018, 14, 6214-6221.