Organic Letters
Letter
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and monoanion 8 of 3 showed λmax at ∼410 and 520 nm,
respectively. Although TDDFT results indicate that 8 has λmax at
∼870 nm, the NIR absorption was not observed due to the
limitation of our instruments. We believe that the modification of
the pyrrole ring of the bisbron complex will open doors to the
development of NIR absorbing dyes having a more red-shifted
absorption and NIR fluorescence dyes.
ASSOCIATED CONTENT
* Supporting Information
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S
Synthetic procedures, UV−vis absorption data, TG−DTA data,
cyclic voltammograms, DFT calculation details, and X-ray crystal
data. The Supporting Information is available free of charge on
AUTHOR INFORMATION
Corresponding Authors
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(9) Kudo, K.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T. Chem.
Commun. 2011, 3867.
Notes
(10) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,
M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K.
N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.;
Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.;
Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa,
J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.;
Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.;
Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.;
Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.;
Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels,
A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.;
Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.;
Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.;
Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham,
M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.;
Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian
09, Revision A. 02; Gaussian, Inc.: Wallingford, CT, 2009.
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Modern Molecular Photochemistry; University Science Books: Sausalito,
1991.
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(14) Unfortunately, the NIR absorption could not be measured due to
the limitation of our instruments.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
This work was partially supported by JSPS KAKENHI
(25870293, Grant-in-Aid for Young Scientists (B)).
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