Enhancing the Potential of Fused Heterocycle-Based Triarylhydrazone Photoswitches
Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
APVV-20-0098
Slovak Research and Development Agency
WA 1850/4-3
Deutsche Forschungsgemeinschaft
ITMS2014+: 313021X329
European Regional Development Fund
ITMS 26230120002
European Regional Development Fund
ITMS 2621012000
European Regional Development Fund
VI.C.212.016
Dutch Research Council (NWO)
PubMed
38212244
DOI
10.1002/chem.202303509
Knihovny.cz E-zdroje
- Klíčová slova
- TD-DFT, hydrazones, photoswitches, thermal stability, transient absorption,
- Publikační typ
- časopisecké články MeSH
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.
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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.
