Enhancing the Potential of Fused Heterocycle-Based Triarylhydrazone Photoswitches.
TD-DFT
hydrazones
photoswitches
thermal stability
transient absorption
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:
24
10
2023
medline:
12
1
2024
pubmed:
12
1
2024
entrez:
11
1
2024
Statut:
aheadofprint
Résumé
Triarylhydrazones represent an attractive class of photochromic compounds offering many interesting features including high molar absorptivity, good addressability, and extraordinary thermal stability. In addition, unlike most other hydrazone-based photoswitches, they effectively absorb light above 365 nm. However, previously prepared triaryhydrazones suffer from low quantum yields of the Z→E photoisomerization. Here, we have designed a new subclass of naphthoyl-benzothiazole hydrazones that balance the most beneficial features of previously reported naphthoyl-quinoline and benzoyl-pyridine triarylhydrazones. These preserve the attractive absorption characteristics, exhibit higher thermal stability of the metastable form than the former and enhance the rate of the Z→E photoisomerization compared to the later, as a result of the weakening of the intramolecular hydrogen bonding between the hydrazone hydrogen and the benzothiazole moiety. Introducing the benzothiazole motif extends the tunability of the photochromic behaviour of hydrazone-based switches.
Identifiants
pubmed: 38212244
doi: 10.1002/chem.202303509
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303509Subventions
Organisme : Slovak Research and Development Agency
ID : APVV-20-0098
Organisme : Deutsche Forschungsgemeinschaft
ID : WA 1850/4-3
Organisme : European Regional Development Fund
ID : ITMS2014+: 313021X329
Organisme : European Regional Development Fund
ID : ITMS 26230120002
Organisme : European Regional Development Fund
ID : ITMS 2621012000
Organisme : Dutch Research Council (NWO)
ID : VI.C.212.016
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
M. Su, Y. Song, Chem. Rev. 2022, 122, 5144-5164.
R. E. Newnham, MRS Bull. 1997, 22, 20-34.
R. M. El-Shishtawy, Int. J. Photoenergy 2009, 2009, 21.
S. Vigneshvar, B. Senthilkumaran, Med. Devices Sens. 2018, 1, e10011.
H. Wang, H. K. Bisoyi, X. Zhang, F. Hassan, Q. Li, Chem. Eur. J. 2022, 28, e202281861.
C. P. Collier, E. W. Wong, M. Belohradský, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394.
S. Erbas-Cakmak, S. Kolemen, A. C. Sedgwick, T. Gunnlaugsson, T. D. James, J. Yoon, E. U. Akkaya, Chem. Soc. Rev. 2018, 47, 2228-2248.
S. Municoy, M. I. Álvarez Echazú, P. E. Antezana, J. M. Galdopórpora, C. Olivetti, A. M. Mebert, M. L. Foglia, M. V. Tuttolomondo, G. S. Alvarez, J. G. Hardy, M. F. Desimone, Int. J. Mol. Sci. 2020, 21, 4724.
M.-M. Russew, S. Hecht, Adv. Mater. 2010, 22, 3348-3360.
J. Boelke, S. Hecht, Adv. Opt. Mater. 2019, 7, 1900404.
K. Matsuda, M. Irie, J. Photochem. Photobiol. 2004, 5, 169-182.
A. Goulet-Hanssens, F. Eisenreich, S. Hecht, Adv. Mater. 2020, 32, 1905966.
E. Orgiu, P. Samorì, Adv. Mater. 2014, 26, 1827-1845.
L. Hou, X. Zhang, G. F. Cotella, G. Carnicella, M. Herder, B. M. Schmidt, M. Pätzel, S. Hecht, F. Cacialli, P. Samorì, Nat. Nanotechnol. 2019, 14, 347-353.
C.-L. Sun, C. Wang, R. Boulatov, ChemPhotoChem 2019, 3, 268-283.
Q. Qiu, S. Yang, M. A. Gerkman, H. Fu, I. Aprahamian, G. G. D. Han, J. Am. Chem. Soc. 2022, 144, 12627-12631.
A. U. Petersen, Z. Wang, P. Erhart, M. B. Nielsen, K. Moth-Poulsen, Nat. Commun. 2018, 9, 1945.
W. A. Velema, W. Szymanski, B. L. Feringa, J. Am. Chem. Soc. 2014, 136, 2178-2191.
M. J. Fuchter, J. Med. Chem. 2020, 63, 11436-11447.
J. Broichhagen, J. A. Frank, D. Trauner, Acc. Chem. Res. 2015, 48, 1947-1960.
M. M. Lerch, M. J. Hansen, G. M. van Dam, W. Szymanski, B. L. Feringa, Angew. Chem. Int. Ed. 2016, 55, 10978-10999.
M. Jeong, J. Park, Y. Seo, K. Lee, S. Pramanik, S. Ahn, S. Kwon, Chem. Eur. J. 2022, 28, e202103972.
M. Zhu, H. Zhou, Org. Biomol. Chem. 2018, 16, 8434-8445.
X. Guo, B. Shao, S. Zhou, I. Aprahamian, Z. Chen, Chem. Sci. 2020, 11, 3016-3021.
X. Su, I. Aprahamian, Chem. Soc. Rev. 2014, 43, 1963-1981.
J. D. Harris, M. J. Moran, I. Aprahamian, Proc. Nat. Acad. Sci. 2018, 115, 9414-9422.
R. Kuhn, W. Münzing, Chem. Ber. 1952, 85, 29-37.
R. Pichon, J. Le Saint, P. Courtot, Tetrahedron 1981, 37, 1517-1524.
H. Qian, S. Pramanik, I. Aprahamian, J. Am. Chem. Soc. 2017, 139, 9140-9143.
B. Shao, H. Qian, Q. Li, I. Aprahamian, J. Am. Chem. Soc. 2019, 141, 8364-8371.
S. Yang, J. D. Harris, A. Lambai, L. L. Jeliazkov, G. Mohanty, H. Zeng, A. Priimagi, I. Aprahamian, J. Am. Chem. Soc. 2021, 143, 16348-16353.
S. Yang, D. Larsen, M. Pellegrini, S. Meier, D. F. Mierke, S. R. Beeren, I. Aprahamian, Chem. 2021, 7, 2190-2200.
M. N. Chaur, D. Collado, J.-M. Lehn, Chem. Eur. J. 2011, 17, 248-258.
D. J. van Dijken, P. Kovaříček, S. P. Ihrig, S. Hecht, J. Am. Chem. Soc. 2015, 137, 14982-14991.
B. Mravec, J. Filo, K. Csicsai, V. Garaj, M. Kemka, A. Marini, M. Mantero, A. Bianco, M. Cigáň, Phys. Chem. Chem. Phys. 2019, 21, 24749-24757.
B. Mravec, Š. Budzák, M. Medveď, L. F. Pašteka, C. Slavov, T. Saßmannshausen, J. Wachtveitl, J. Kožíček, L. Hegedüsová, J. Filo, M. Cigáň, J. Org. Chem. 2021, 86, 11633-11646.
B. Shao, I. Aprahamian, ChemistryOpen 2020, 9, 191-194.
N. Mardirossian, M. Head-Gordon, Mol. Phys. 2017, 115, 2315-2372.
K. Spiekermann, L. Pattanaik, W. H. Green, Sci. Data 2022, 9, 417.
T. Le Bahers, C. Adamo, I. Ciofini, J. Chem. Theory Comput. 2011, 7, 2498-2506.
D. Jacquemin, T. L. Bahers, C. Adamo, I. Ciofini, Phys. Chem. Chem. Phys. 2012, 14, 5383-5388.
B. Mravec, A. Marini, M. Tommasini, J. Filo, M. Cigáň, M. Mantero, S. Tosi, M. Canepa, A. Bianco, ChemPhysChem 2021, 22, 533-541.
T. Petrenko, F. Neese, J. Chem. Phys. 2007, 127, 164319.
F. Neese, ORCA, an ab initio, density functional and semiempirical SCF-MO package, version 2.9.
C. Slavov, H. Hartmann, J. Wachtveitl, Anal. Chem. 2015, 87, 2328-2336.
C. Slavov, C. Boumrifak, C. A. Hammer, P. Trojanowski, X. Chen, W. J. Lees, J. Wachtveitl, M. Braun, Phys. Chem. Chem. Phys. 2016, 18, 10289-10296.
S. Lee, M. Filatov, S. Lee, C. H. Choi, J. Chem. Phys. 2018, 149, 104101.
G. M. J. Barca, C. Bertoni, L. Carrington, D. Datta, N. De Silva, J. E. Deustua, D. G. Fedorov, J. R. Gour, A. O. Gunina, E. Guidez, T. Harville, S. Irle, J. Ivanic, K. Kowalski, S. S. Leang, H. Li, W. Li, J. J. Lutz, I. Magoulas, J. Mato, V. Mironov, H. Nakata, B. Q. Pham, P. Piecuch, D. Poole, S. R. Pruitt, A. P. Rendell, L. B. Roskop, K. Ruedenberg, T. Sattasathuchana, M. W. Schmidt, J. Shen, L. Slipchenko, M. Sosonkina, V. Sundriyal, A. Tiwari, J. L. Galvez Vallejo, B. Westheimer, M. Wloch, P. Xu, F. Zahariev, M. S. Gordon, J. Chem. Phys. 2020, 152, 154102.
A. Gáplovský, Š. Toma, J. Donovalová, J. Photochem. Photobiol., A 2007, 191, 162-166.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian ~16 Revision C.01, 2016, Gaussian Inc. Wallingford CT.
F. Weigend, Phys. Chem. Chem. Phys. 2006, 8, 1057-1065.
T. Yanai, D. Tew, N. Handy, Chem. Phys. Lett. 2004, 393, 51-57.
Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241.
H. S. Yu, X. He, S. L. Li, D. G. Truhlar, Chem. Sci. 2016, 7, 5032-5051.
S. Miertuš, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117-129.
J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3094.
M. Cossi, V. Barone, J. Chem. Phys. 2001, 115, 4708-4717.
R. Cammi, B. Mennucci, J. Chem. Phys. 1999, 110, 9877-9886.
M. Caricato, B. Mennucci, J. Tomasi, F. Ingrosso, R. Cammi, S. Corni, G. Scalmani, J. Chem. Phys. 2006, 124, 124520.
Y.-P. Li, J. Gomes, S. Mallikarjun Sharada, A. T. Bell, M. Head-Gordon, J. Phys. Chem. C 2015, 119, 1840-1850.
R. F. Ribeiro, A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2011, 115, 14556-14562.
G. Luchini, J. Alegre-Requena, I. Funes-Ardoiz, R. Paton, F1000Research 2020, 9.
M. Drobizhev, N. S. Makarov, S. E. Tillo, T. E. Hughes, A. Rebane, J. Phys. Chem. B 2012, 116, 1736-1744.
S. Maeda, K. Ohno, K. Morokuma, J. Chem. Theory Comput. 2010, 6, 1538-1545.