Bright White-Light Emission from a Single Organic Compound in the Solid State†
Dr. Qing-Yuan Yang
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)
Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, Strasbourg 67000 (France)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jean-Marie Lehn
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)
Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, Strasbourg 67000 (France)
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)===Search for more papers by this authorDr. Qing-Yuan Yang
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)
Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, Strasbourg 67000 (France)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jean-Marie Lehn
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)
Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, Strasbourg 67000 (France)
Lehn Institute of Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (China)===Search for more papers by this authorWe thank Chien-Wei Hsu for time-resolved fluorescence measurements, Corinne Bailly for the crystal-structure determination, and Dr. Laura Maggini for the SEM imaging. We also thank Prof. Bernard Valeur for helpful comments. Q.-Y.Y. thanks the China Postdoctoral Science Foundation (2012M510203, 2013T60819), the Leading Talent Project in Guangdong Province (31000-3210003), and the 973 Program of China (2012CB821701) for financial support. This research was supported in part by the ANR-10-BLAN-717.
Abstract
White-light-emitting materials and devices have attracted enormous interest because of their great potential for various lighting applications. We herein describe the light-emitting properties of a series of new difunctional organic molecules of remarkably simple structure consisting of two terminal 4-pyridone push–pull subunits separated by a polymethylene chain. They were found to emit almost “pure” white light as a single organic compound in the solid state, as well as when incorporated in a polymer film. To the best of our knowledge, they are the simplest white-light-emitting organic molecules reported to date.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange_201400155_sm_miscellaneous_information.pdf2.2 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aG. M. Farinola, R. Ragni, Chem. Soc. Rev. 2011, 40, 3467–3482;
- 1bB. W. D’Andrade, S. R. Forrest, Adv. Mater. 2004, 16, 1585–1595;
- 1cC. Ulbricht, B. Beyer, C. Friebe, A. Winter, U. S. Schubert, Adv. Mater. 2009, 21, 4418–4441;
- 1dS. C. F. Kui, P. K. Chow, G. S. M. Tong, S. L. Lai, G. Cheng, C. C. Kwok, K. H. Low, M. Y. Ko, C. M. Che, Chem. Eur. J. 2013, 19, 69–73;
- 1eH. C. Su, H. F. Chen, F. C. Fang, C. C. Liu, C. C. Wu, K. T. Wong, Y. H. Liu, S. M. Peng, J. Am. Chem. Soc. 2008, 130, 3413–3419;
- 1fB. H. Zhang, G. P. Tan, C. S. Lam, B. Yao, C. L. Ho, L. H. Liu, Z. Y. Xie, W. Y. Wong, J. Q. Ding, L. X. Wang, Adv. Mater. 2012, 24, 1873–1877;
- 1gV. K. Praveen, C. Ranjith, N. Armaroli, Angew. Chem. 2014, 126, 373–376;
10.1002/ange.201306787 Google ScholarAngew. Chem. Int. Ed. 2014, 53, 365–368;
- 1hB. D’Andrade, M. E. Thompson, S. R. Forrest, Adv. Mater. 2002, 14, 147–151.
- 2
- 2aG. L. Tu, C. Y. Mei, Q. G. Zhou, Y. X. Cheng, Y. H. Geng, L. X. Wang, D. G. Ma, X. B. Jing, F. S. Wang, Adv. Funct. Mater. 2006, 16, 101–106;
- 2bB. P. Yan, C. C. C. Cheung, S. C. F. Kui, H. F. Xiang, V. A. L. Roy, S. J. Xu, C. M. Che, Adv. Mater. 2007, 19, 3599–3603;
- 2cB. W. D’Andrade, R. J. Holmes, S. R. Forrest, Adv. Mater. 2004, 16, 624–628.
- 3
- 3aP. Coppo, M. Duati, V. N. Kozhevnikov, J. W. Hofstraat, L. De Cola, Angew. Chem. 2005, 117, 1840–1844;
10.1002/ange.200461953 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 1806–1810;
- 3bA. H. Shelton, I. V. Sazanovich, J. A. Weinstein, M. D. Ward, Chem. Commun. 2012, 48, 2749–2751;
- 3cH. J. Bolink, F. De Angelis, E. Baranoff, C. Klein, S. Fantacci, E. Coronado, M. Sessolo, K. Kalyanasundaram, M. Gratzel, M. K. Nazeeruddin, Chem. Commun. 2009, 4672–4674;
- 3dD. Sykes, I. S. Tidmarsh, A. Barbieri, I. V. Sazanovich, J. A. Weinstein, M. D. Ward, Inorg. Chem. 2011, 50, 11323–11339;
- 3eG. L. Law, K. L. Wong, H. L. Tam, K. W. Cheah, W. T. Wong, Inorg. Chem. 2009, 48, 10492–10494;
- 3fG. J. He, D. Guo, C. He, X. L. Zhang, X. W. Zhao, C. Y. Duan, Angew. Chem. 2009, 121, 6248–6251; Angew. Chem. Int. Ed. 2009, 48, 6132–6135;
- 3gV. Adamovich, J. Brooks, A. Tamayo, A. M. Alexander, P. I. Djurovich, B. W. D’Andrade, C. Adachi, S. R. Forrest, M. E. Thompson, New J. Chem. 2002, 26, 1171–1178.
- 4
- 4aY. Yang, M. Lowry, C. M. Schowalter, S. O. Fakayode, J. O. Escobedo, X. Xu, H. Zhang, T. J. Jensen, F. R. Fronczek, I. M. Warner, R. M. Strongin, J. Am. Chem. Soc. 2006, 128, 14081–14092;
- 4bS. Park, J. E. Kwon, S. H. Kim, J. Seo, K. Chung, S. Y. Park, D. J. Jang, B. M. Medina, J. Gierschner, S. Y. Park, J. Am. Chem. Soc. 2009, 131, 14043–14049;
- 4cK. C. Tang, M. J. Chang, T. Y. Lin, H. A. Pan, T. C. Fang, K. Y. Chen, W. Y. Hung, Y. H. Hsu, P. T. Chou, J. Am. Chem. Soc. 2011, 133, 17738–17745;
- 4dY. Liu, M. Nishiura, Y. Wang, Z. M. Hou, J. Am. Chem. Soc. 2006, 128, 5592–5593;
- 4eP. Nandhikonda, D. Heagy, Chem. Commun. 2010, 46, 8002–8004;
- 4fJ. Y. Li, D. Liu, C. Ma, O. Lengyel, C. S. Lee, C. H. Tung, S. T. Lee, Adv. Mater. 2004, 16, 1538–1541;
- 4gfor white-light emission from a two-component micellar system, see X. Zhang, D. Görl, F. Würthner, Chem. Commun. 2013, 49, 8178–8180.
- 5S. K. Freeman, W. F. Ringk, P. E. Spoerri, J. Am. Chem. Soc. 1947, 69, 858–859.
- 6A. Das, J. C. Jeffery, J. P. Maher, J. A. McCleverty, E. Schatz, M. D. Ward, G. Wollermann, Angew. Chem. 1992, 104, 1554–1556; Angew. Chem. Int. Ed. Engl. 1992, 31, 1515–1518.
- 7V. Diemer, H. Chaumeil, A. Defoin, P. Jacquesb, C. Carre, Tetrahedron Lett. 2005, 46, 4737–4740.
- 8R. M. Acheson, E. C. Constable, J. Chem. Soc. Chem. Commun. 1980, 1065–1066.
- 9L. Johnson, Y. Kitahara, T. J. R. Weakley, J. F. W. Keana, Tetrahedron Lett. 1993, 34, 5555–5558.
- 10H. Vorbrüggen, K. Krolikiewicz, Chem. Ber. 1984, 117, 1523–1541.
- 11A molecule containing three 4-hydroxypyridine/4-pyridone groups was prepared in the course of an exploration of potential multivalent ligands for luminescent rare-earth metal cations, see Q. Y. Yang, K. Li, J. Luo, M. Pan, C. Y. Su, Chem. Commun. 2011, 47, 4234–4236.
- 12For a study of emission from an excited oligomer of stacked anthracene molecules in the solid state, see T. Hinoue, Y. Shigenoi, M. Sugino, Y. Mizobe, I. Hisaki, M. Miyata, N. Tohnai, Chem. Eur. J. 2012, 18, 4634–4643.
- 13For a presentation of excimers, see B. Valeur, Molecular Fluorescence: Principles and Applications, Wiley-VCH, Weinheim, 2002, pp. 94–98.
- 14For studies on excimers, see
- 14aA. D. Q. Li, W. Wang, L. Q. Wang, Chem. Eur. J. 2003, 9, 4594–4601;
- 14bH. Yoo, J. Yang, A. Yousef, M. R. Wasielewski, D. Kim, J. Am. Chem. Soc. 2010, 132, 3939–3944;
- 14cJ. M. Giaimo, J. V. Lockard, L. E. Sinks, A. M. Scott, T. M. Wilson, M. R. Wasielewski, J. Phys. Chem. A 2008, 112, 2322–2330;
- 14dF. Würthner, C. Thalacker, S. Diele, C. Tschierske, Chem. Eur. J. 2001, 7, 2245–2253.
10.1002/1521-3765(20010518)7:10<2245::AID-CHEM2245>3.0.CO;2-W CAS PubMed Web of Science® Google Scholar
- 15For intramolecular excimers, see also
- 15aK. Zachariasse, W. Kühnle, Z. Phys. Chem. Neue Folge 1976, 101, 267;
- 15bM. A. Winnik, Chem. Rev. 1981, 81, 491–524;
- 15cF. C. De Schryver, P. Collart, J. Vandendriessche, R. Goedeweeck, A. Swinnen, M. Van der Auweraer, Acc. Chem. Res. 1987, 20, 159–166;
- 15dF. M. Winnik, Chem. Rev. 1993, 93, 587–614.
- 16A. Neelakantan, R. Stine, J. K. Maranas, Macromolecules 2003, 36, 3721–3731.
- 17D. Kim, J. L. Bredas, J. Am. Chem. Soc. 2009, 131, 11371–11380.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.