Crystal-to-Gel Transformation Stimulated by a Solid-State E→Z Photoisomerization.
crystals
gels
isomerization
magnetism
photochemistry
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
21 Oct 2019
21 Oct 2019
Historique:
received:
14
06
2019
revised:
07
08
2019
pubmed:
10
8
2019
medline:
10
8
2019
entrez:
10
8
2019
Statut:
ppublish
Résumé
The molecule (E)-(5-(3-anthracen-9-yl-allylidene)-2,2-dimethyl-[1,3] dioxane-4,6-dione) (E-AYAD) undergoes E→Z photoisomerization. In the solid state, this photoisomerization process can initiate a physical transformation of the crystal that is accompanied by a large volume expansion (ca. 10 times), loss of crystallinity, and growth of large pores. This physical change requires approximately 10 % conversion of the E isomer to the Z isomer and results in a gel-like solid with decreased stiffness that still retains its mechanical integrity. The induced porosity allows the expanding gel to engulf superparamagnetic nanoparticles from the surrounding liquid. The trapped superparamagnetic nanoparticles impart a magnetic susceptibility to the gel, allowing it to be moved by a magnetic field. The photoinduced phase transition, starting with a compact crystalline solid instead of a dilute solution, provides a new route for in situ production of functional porous materials.
Identifiants
pubmed: 31397530
doi: 10.1002/anie.201907454
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
15429-15434Subventions
Organisme : National Science Foundation
ID : DMR-1810514
Organisme : National Science Foundation
ID : PHY-1607749
Organisme : National Science Foundation
ID : CHE-0541848
Organisme : King Abdullah International Medical Research Center
ID : RC10/104
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
P. Naumov, S. Chizhik, M. K. Panda, N. K. Nath, E. Boldyreva, Chem. Rev. 2015, 115, 12440-12490;
J. M. Abendroth, O. S. Bushuyev, P. S. Weiss, C. J. Barrett, ACS Nano 2015, 9, 7746-7768;
Q. Yu, B. Aguila, J. Gao, P. Xu, Q. Chen, J. Yan, D. Xing, Y. Chen, P. Cheng, Z. Zhang, S. Ma, Chem. Eur. J. 2019, 25, 5611-5622.
N. K. Nath, L. Pejov, S. M. Nichols, C. Hu, N. Saleh, B. Kahr, P. Naumov, J. Am. Chem. Soc. 2014, 136, 2757-2766;
T. Kim, L. Zhu, L. J. Mueller, C. J. Bardeen, J. Am. Chem. Soc. 2014, 136, 6617-6625;
T. Kim, L. Zhu, R. O. Al-Kaysi, C. J. Bardeen, ChemPhysChem 2014, 15, 400-414;
T. J. White, Photomechanical Materials, Composites, and Systems: Wireless Transduction of Light into Work, 1st ed., Wiley, Hoboken, 2017.
R. O. Al-Kaysi, A. M. Muller, C. J. Bardeen, J. Am. Chem. Soc. 2006, 128, 15938-15939;
S. Kobatake, S. Takami, H. Muto, T. Ishikawa, M. Irie, Nature 2007, 446, 778-781;
M. Morimoto, M. Irie, J. Am. Chem. Soc. 2010, 132, 14172-14178;
H. Koshima, N. Ojima, H. Uchimoto, J. Am. Chem. Soc. 2009, 131, 6890-6891;
H. Koshima, K. Takechi, H. Uchimoto, M. Shiro, D. Hashizume, Chem. Commun. 2011, 47, 11423-11425;
P. Naumov, J. Kowalik, K. M. Solntsev, A. Baldridge, J.-S. Moon, C. Kranz, L. M. Tolbert, J. Am. Chem. Soc. 2010, 132, 5845-5857;
R. Medishetty, A. Husain, Z. Bai, T. Runceviski, R. E. Dinnebier, P. Naumov, J. J. Vittal, Angew. Chem. Int. Ed. 2014, 53, 5907-5911;
Angew. Chem. 2014, 126, 6017-6021;
O. S. Bushuyev, A. Tomberg, T. Friscic, C. J. Barrett, J. Am. Chem. Soc. 2013, 135, 12556-12559;
J. K. Sun, W. Li, C. Chen, C. X. Ren, D. M. Pan, J. Zhang, Angew. Chem. Int. Ed. 2013, 52, 6653-6657;
Angew. Chem. 2013, 125, 6785-6789;
D. Kitagawa, H. Tsujioka, F. Tong, X. Dong, C. J. Bardeen, S. Kobatake, J. Am. Chem. Soc. 2018, 140, 4208-4212;
Q. Yu, X. Yang, Y. Chen, K. Yu, J. Gao, Z. Liu, P. Cheng, Z. Zhang, B. Aguila, S. Ma, Angew. Chem. Int. Ed. 2018, 57, 10192-10196;
Angew. Chem. 2018, 130, 10349-10353.
T. Kim, M. K. Al-Muhanna, S. D. Al-Suwaidan, R. O. Al-Kaysi, C. J. Bardeen, Angew. Chem. Int. Ed. 2013, 52, 6889-6893;
Angew. Chem. 2013, 125, 7027-7031.
F. Tong, M. Liu, R. O. Al-Kaysi, C. J. Bardeen, Langmuir 2018, 34, 1627-1634.
F. Tong, M. Al-Haidar, L. Zhu, R. O. Al-Kaysi, C. J. Bardeen, Chem. Commun. 2019, 55, 3709-3712.
M. J. R. Reddy, P. A. Kumar, U. Srinivas, V. V. Reddy, M. J. R. Reddy, G. V. Rao, V. J. Rao, Indian J. Chem. Sect. B 2007, 46, 1833-1847.
G. M. J. Schmidt, Pure Appl. Chem. 1971, 27, 647-678;
V. Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433-481.
M. K. Maurer, I. K. Lednev, S. A. Asher, Adv. Funct. Mater. 2005, 15, 1401-1406;
J. Liu, J. Nie, Y. Zhao, Y. He, J. Photochem. Photobiol. A 2010, 211, 20-25.
S. Miljanić, L. Frkanec, Z. Meić, M. Žinić, Langmuir 2005, 21, 2754-2760;
M. Akazawa, K. Uchida, J. J. D. de Jong, J. Areephong, M. Stuart, G. Caroli, W. R. Browne, B. L. Feringa, Org. Biomol. Chem. 2008, 6, 1544-1547;
Y.-L. Zhao, J. F. Stoddart, Langmuir 2009, 25, 8442-8446;
Y. Wu, S. Wu, X. Tian, X. Wang, W. Wu, G. Zou, Q. Zhang, Soft Matter 2011, 7, 716-721.
C. Bernades, M. Carravetta, S. J. Coles, E. R. H. van Eck, H. Meekes, M. E. Minas da Piedade, M. B. Pitak, M. Podmore, T. A. H. de Ruiter, L.-C. Söğütoğlu, R. R. E. Steendam, T. Threlfall, Cryst. Growth Des. 2019, 19, 907-917.
R. Yu, N. Lin, W. Yu, X. Y. Liu, CrystEngComm 2015, 17, 7986-8010.
M. L. Juan, J. Plain, R. Bachelot, P. Royer, S. K. Gray, G. P. Wiederrecht, Appl. Phys. Lett. 2008, 93, 153304.
F. Geng, R. Ma, A. Nakamura, K. Akatsuka, Y. Ebina, Y. Yamauchi, N. Miyamoto, Y. Tateyama, T. Sasaki, Nat. Commun. 2013, 4, 1632;
L. Zhang, J. B. Bailey, R. H. Subramanian, F. A. Tezcan, Nature 2018, 557, 86-91.
A. R. Hirst, I. A. Coates, T. R. Boucheteau, J. F. Miravet, B. Escuder, V. Castelletto, I. W. Hamley, D. K. Smith, J. Am. Chem. Soc. 2008, 130, 9113-9121.
J. Ge, Y. Hu, Y. Yin, Angew. Chem. Int. Ed. 2007, 46, 7428-7431;
Angew. Chem. 2007, 119, 7572-7575;
F. Tong, W. Xu, M. Al-Haidar, D. Kitagawa, R. O. Al-Kaysi, C. J. Bardeen, Angew. Chem. Int. Ed. 2018, 57, 7080-7084;
Angew. Chem. 2018, 130, 7198-7202.
M. X. Wu, J. Gao, F. Wang, J. Yang, N. Song, X. Jin, P. Mi, J. Tian, J. Luo, F. Liang, Y. W. Yang, Small 2018, 14, 1704440.