Polysubstituted 5-Phenylazopyrimidines: Extremely Fast Non-ionic Photochromic Oscillators.
DFT calculations
azopyrimidines
photochromic oscillators
ultrafast spectroscopy
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:
01 Sep 2020
01 Sep 2020
Historique:
received:
15
05
2020
pubmed:
21
5
2020
medline:
21
5
2020
entrez:
21
5
2020
Statut:
ppublish
Résumé
Photochromic systems with an ultrahigh rate of thermal relaxation are highly desirable for the development of new efficient photochromic oscillators. Based on DFT calculations, we designed a series of 5-phenylazopyrimidines with strong push-pull character in silico and observed very low energy barriers for the thermal (Z)-to-(E) isomerization. The structure of the (Z)-isomer of the slowest isomerizing derivative in the series was confirmed by NMR analysis with in situ irradiation at low temperature. The substituents can tune the lifetime of thermal back isomerization from hundreds of microseconds to several nanoseconds (8 orders of magnitude). The photoswitching parameters were extracted from transient absorption techniques and a dominant rotation mechanism of the (Z)-to-(E) thermal fading was proposed based on DFT calculations.
Identifiants
pubmed: 32433814
doi: 10.1002/anie.202007065
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15590-15594Subventions
Organisme : Grantová Agentura České Republiky
ID : 18-11851S
Organisme : Deutsche Forschungsgemeinschaft
ID : WA 1850/4-2
Organisme : Center for Urban Science and Progress
ID : ITMS 26240220086
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
S. Erbas-Cakmak, D. A. Leigh, C. T. McTernan, A. L. Nussbaumer, Chem. Rev. 2015, 115, 10081-10206;
F. Lancia, A. Ryabchun, N. Katsonis, Nat. Rev. Chem. 2019, 3, 536-551;
W. A. Velema, W. Szymanski, B. L. Feringa, J. Am. Chem. Soc. 2014, 136, 2178-2191;
R. Göstl, A. Senf, S. Hecht, Chem. Soc. Rev. 2014, 43, 1982-1996;
S. Steinwand, Z. L. Yu, S. Hecht, J. Wachtveitl, J. Am. Chem. Soc. 2016, 138, 12997-13005.
H. M. Bandara, S. C. Burdette, Chem. Soc. Rev. 2012, 41, 1809-1825;
S. Crespi, N. A. Simeth, B. Konig, Nat. Rev. Chem. 2019, 3, 133-146.
M. Klok, N. Boyle, M. T. Pryce, A. Meetsma, W. R. Browne, B. L. Feringa, J. Am. Chem. Soc. 2008, 130, 10484-10485.
J. Garcia-Amorós, S. Nonell, D. Velasco, Chem. Commun. 2012, 48, 3421-3423.
U. A. Hrozhyk, S. V. Serak, N. V. Tabiryan, T. J. White, T. J. Bunning, Opt. Express 2010, 18, 9651-9657.
J. D. Harris, M. J. Moran, I. Aprahamian, Proc. Natl. Acad. Sci. USA 2018, 115, 9414-9422;
J. Wachtveitl, T. Nägele, B. Puell, W. Zinth, M. Krüger, S. Rudolph-Böhner, D. Oesterhelt, L. Moroder, J. Photochem. Photobiol. A 1997, 105, 283-288.
P. J. Coelho, C. M. Sousa, M. C. R. Castro, A. M. C. Fonseca, M. M. M. Raposo, Opt. Mater. 2013, 35, 1167-1172;
J. Garcia-Amorós, M. Reig, M. C. Castro, A. Cuadrado, M. M. Raposo, D. Velasco, Chem. Commun. 2014, 50, 6704-6706;
J. Garcia-Amorós, D. Velasco, Beilstein J. Org. Chem. 2012, 8, 1003-1017;
J. Calbo, C. E. Weston, A. J. White, H. S. Rzepa, J. Contreras-Garcia, M. J. Fuchter, J. Am. Chem. Soc. 2017, 139, 1261-1274;
N. A. Simeth, S. Crespi, M. Fagnoni, B. Konig, J. Am. Chem. Soc. 2018, 140, 2940-2946;
C. Slavov, C. Yang, A. H. Heindl, H. A. Wegner, A. Dreuw, J. Wachtveitl, Angew. Chem. Int. Ed. 2020, 59, 380-387;
Angew. Chem. 2020, 132, 388-395.
P. J. Coelho, M. C. R. Castro, A. M. C. Fonseca, M. M. M. Raposo, Dyes Pigm. 2012, 92, 745-748.
J. Garcia-Amóros, A. Bučinskas, M. Reig, S. Nonell, D. Velasco, J. Mater. Chem. C 2014, 2, 474-480;
J. Garcia-Amóros, B. Maerz, M. Reig, A. Cuadrado, L. Blancafort, E. Samoylova, D. Velasco, Chem. Eur. J. 2019, 25, 7726-7732.
J. Garcia-Amóros, M. C. R. Castro, P. Coelho, M. M. M. Raposo, D. Velasco, Chem. Commun. 2016, 52, 5132-5135;
J. Garcia-Amóros, M. Diaz-Lobo, S. Nonell, D. Velasco, Angew. Chem. Int. Ed. 2012, 51, 12820-12823;
Angew. Chem. 2012, 124, 12992-12995.
S. Crespi, N. A. Simeth, A. Bellisario, M. Fagnoni, B. Konig, J. Phys. Chem. A 2019, 123, 1814-1823.
E. Procházková, L. Čechová, J. Kind, Z. Janeba, C. M. Thiele, M. Dračínský, Chem. Eur. J. 2018, 24, 492-498;
L. Čechová, J. Kind, M. Dračínský, J. Filo, Z. Janeba, C. M. Thiele, M. Cigáň, E. Procházková, J. Org. Chem. 2018, 83, 5986-5998.
R. F. Quijano-Quiñones, M. Quesadas-Rojas, G. Cuevas, G. J. Mena-Rejón, Molecules 2012, 17, 4661-4671.
C. Slavov, H. Hartmann, J. Wachtveitl, Anal. Chem. 2015, 87, 2328-2336.
T. Nägele, R. Hoche, W. Zinth, J. Wachtveitl, Chem. Phys. Lett. 1997, 272, 489-495;
P. Hamm, S. M. Ohline, W. Zinth, J. Chem. Phys. 1997, 106, 519-529;
C. Slavov, C. Yang, L. Schweighauser, C. Boumrifak, A. Dreuw, H. A. Wegner, J. Wachtveitl, Phys. Chem. Chem. Phys. 2016, 18, 14795-14804;
A. Nenov, R. Borrego-Varillas, A. Oriana, L. Ganzer, F. Segatta, I. Conti, J. Segarra-Marti, J. Omachi, M. Dapor, S. Taioli, C. Manzoni, S. Mukamel, G. Cerullo, M. Garavelli, J. Phys. Chem. Lett. 2018, 9, 1534-1541.
B. Schmidt, C. Sobotta, S. Malkmus, S. Laimgruber, M. Braun, W. Zinth, P. Gilch, J. Phys. Chem. A 2004, 108, 4399-4404;
F. O. Koller, C. Sobotta, T. E. Schrader, T. Cordes, W. J. Schreier, A. Sieg, P. Gilch, Chem. Phys. 2007, 341, 258-266;
J. Bahrenburg, K. Rottger, R. Siewertsen, F. Renth, F. Temps, Photochem. Photobiol. Sci. 2012, 11, 1210-1219.