10.1002/chem.201904900
Chemistry - A European Journal
RESEARCH ARTICLE
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Chen, W.; Chen, C. L.; Zhang, Z. Y.; Chen, Y. A.; Chao, W. C.; Su, J.
H.; Tian, H.; Chou, P. T., Snapshotting the Excited-State Planarization
Fluorescence up-conversion data were fitted to the sum of exponential
functions convoluted with the instrument response function (IRF). The
IRF was determined from the Raman scattering signal, and its profile was
fitted to a Gaussian function with a full width at half maximum of 220 fs.
of
Chemically
Locked
N,N’-Disubstituted
Dihydrodibenzo[a,c]phenazines. J. Am. Chem. Soc. 2017, 139, 1636-
1644.
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Zhang, Z. Y.; Chen, C. L.; Chen, Y. A.; Wei, Y. C.; Su, J. H.; Tian, H.;
Chou, P. T., Tuning the Conformation and Color of Conjugated
Polyheterocyclic Skeletons by Installing ortho-Methyl Groups. Angew.
Chem. Int. Ed. 2018, 57, 9880-9884.
Associated Content
Humeniuk, H. V.; Rosspeintner, A.; Licari, G.; Kilin, V.; Bonacina, L.;
Vauthey, E.; Sakai, N.; Matile, S., White-Fluorescent Dual-Emission
Mechanosensitive Membrane Probes that Function by Bending Rather
than Twisting. Angew. Chem. Int. Ed. 2018, 57, 10559-10563.
Chen, D. G.; Lin, T. C.; Chen, C. L.; Chen, Y. T.; Chen, Y. A.; Lee, G.
H.; Chou, P. T.; Liao, C. W.; Chiu, P.C.; Chang, C. H.; Lien, Y. J.; Chi,
Y., Optically Triggered Planarization of Boryl-Substituted Phenoxazine:
Another Horizon of TADF Molecules and High-Performance OLEDs.
ACS Appl. Mater. Inter. 2018, 10, 12886-12896.
Supporting Information. The supporting information is available free
of charge via the Internet. Synthetic methods for the compounds, NMR,
and computational details are provided.
Crystallographic data. The X-ray crystallographic coordinates for the
compounds reported in this article has been deposited at the Cambridge
Crystallographic Data Centre (CCDC) under deposition number CCDC
1688839 (PNO), 1552393 (PNS), 1588837 (PNSe) and 1878212 (PNC).
These data can be obtained free of charge from The Cambridge
[9]
Zhou, Z.; Chen, D. G.; Saha, M. L.; Wang, H.; Li, X.; Chou, P. T.; Stang,
P. J., Designed Conformation and Fluorescence Properties of Self-
Assembled Phenazine-Cored Platinum(II) Metallacycles. J. Am. Chem.
Soc. 2019, 141, 5535-5543.
[10] Yang, J.; Qin, J. W.; Geng, P. Y.; Wang, J. Q.; Fang, M. M.; Li, Z.,
Molecular Conformation-Dependent Mechanoluminescence: Same
Mechanical Stimulus but Different Emissive Color over Time. Angew
Chem. Int. Ed. 2018, 57, 14174-14178.
Acknowledgements
P.-T. Chou thanks for the financial supports from Ministry of Science and
Technology (MOST), featured areas research program within the
framework of the Higher Education Sprout Project administrated by
Ministry of Education (MOE) of Taiwan. H. T. thanks financial support by
NSFC/China (21788102). We are grateful to the National Center for the
High-performance Computing (NCHC) of Taiwan for the valuable
computer time and facilities.
[11] Grabner, G.; Rechthaler, K.; Köhler, G., Picosecond Excited-State
Solvation Dynamics of 9,9'-Bianthryl in Alcohol Solutions. J. Phys.
Chem. A 1998, 102, 689-696.
[12] Baumgarten, M.; Gherghel, L.; Friedrich, J.; Jurczok, M.; Rettig, W.,
Electronic Decoupling in Ground and Excited States of Asymmetric
Biaryls. J. Phys. Chem. A 2000, 104, 1130-1140.
[13] Haberhauer, G., Planarized and twisted intramolecular charge transfer:
a
concept for fluorophores showing two independent rotations in
excited state. Chem. Eur. J. 2017, 23, 9288-9296.
Conflict of interest
[14] Sension, R. J.; Repinec, S. T.; Szarka, A. Z.; Hochstrasser, R. M.,
Femtosecond laser studies of the cis-stilbene photoisomerization
reactions. J. Chem. Phys. 1993, 98, 6291-6315.
The authors declare no conflict of interest.
[15] Dugave, C.; Demange, L., Cis-Trans Isomerization of Organic
Molecules and Biomolecules:ꢀ Implications and Applications. Chem.
Rev. 2003, 103, 2475-2532.
Keywords: Photoinduced structural planarization, heteroatom
substitution effect, large Stokes shifted emission, mono-heteroatom
[16] Grebel-Koehler, D.; Liu, D.; De Feyter, S.; Enkelmann, V.; Weil, T.;
Engels, C.; Samyn, C.; Müllen, K.; De Schryver, F. C., Synthesis and
photomodulation of rigid polyphenylene dendrimers with an
azobenzene core. Macromolecules, 2003, 36, 578-590.
substituted
dihydrodibenzo[a,c]phenazines,
bent
heterocyclic
conformation, fluorescence up-conversion
[17] Pande, K.; Hutchison, C. D. M.; Groenhof, G.; Aquila, A.; Robinson, J.
S.; Tenboer, J.; Basu, S.; Boutet, S.; DePonte, D. P.; Liang, M. N.;
White, T. A.; Zatsepin, N. A.; Yefanov, O.; Morozov, D.; Oberthuer, D.;
Gati, C.; Subramanian, G.; James, D.; Zhao, Y.; Koralek, J.; Brayshaw,
J.; Kupitz, C.; Conrad, C.; Roy-Chowdhury, S.; Coe, J. D.; Metz, M.;
Xavier, P. L.; Grant, T. D.; Koglin, J. E.; Ketawala, G.; Fromme, R.;
Srajer, V.; Henning, R.; Spence, J. C. H.; Ourmazd, A.; Schwander, P.;
Weierstall, U.; Frank, M.; Fromme, P.; Barty, A.; Chapman, H. N.;
Moffat, K.; van Thor, J. J.; Schmidt, M., Femtosecond structural
dynamics drives the trans/cis isomerization in photoactive yellow
protein. Science 2016, 352, 725-729.
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