Luminescent Pincer Platinum(II) Complexes with Emission Quantum Yields up to Almost Unity: Photophysics, Photoreductive CC Bond Formation, and Materials Applications†
Dr. Pui-Keong Chow
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Gang Cheng
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Glenna So Ming Tong
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Wai-Pong To
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorWai-Lun Kwong
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Kam-Hung Low
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Chi-Chung Kwok
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Chensheng Ma
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Ming Che
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
HKU Shenzhen Institute of Research and Innovation, Shenzhen 518053 (China)
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)Search for more papers by this authorDr. Pui-Keong Chow
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Gang Cheng
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Glenna So Ming Tong
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Wai-Pong To
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorWai-Lun Kwong
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Kam-Hung Low
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Chi-Chung Kwok
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorDr. Chensheng Ma
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Ming Che
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)
HKU Shenzhen Institute of Research and Innovation, Shenzhen 518053 (China)
State Key Laboratory of Synthetic Chemistry, Institute of Molecular Functional Materials, HKU-CAS Joint Laboratory on New Materials, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P.R. China)Search for more papers by this authorThis work was supported by the Hong Kong Research Grants Council (HKU 700812P), the CAS-Croucher Foundation Funding Scheme for Joint Laboratories, the Area of Excellence Program (AoE/P-03/08), the National Key Basic Research Program of China (2013CB834802), and the Guangdong Special Project of the Introduction of Innovative R&D Teams, China. We are thankful for the assistance of The University of Hong Kong Li Ka Shing Faculty of Medicine Faculty Core Facility for use of the laser scan confocal microscope.
Abstract
Luminescent pincer-type PtII complexes supported by C-deprotonated π-extended tridentate RC^N^NR′ ligands and pentafluorophenylacetylide ligands show emission quantum yields up to almost unity. Femtosecond time-resolved fluorescence measurements and time-dependent DFT calculations together reveal the dependence of excited-state structural distortions of [Pt(RC^N^NR′)(CC-C6F5)] on the positional isomers of the tridentate ligand. Pt complexes [Pt(R-C^N^NR′)(CC-Ar)] are efficient photocatalysts for visible-light-induced reductive CC bond formation. The [Pt(R-C^N^NR′)(CC-C6F5)] complexes perform strongly as phosphorescent dopants for green- and red-emitting organic light-emitting diodes (OLEDs) with external quantum efficiency values over 22.1 %. These complexes are also applied in two-photon cellular imaging when incorporated into mesoporous silica nanoparticles (MSNs).
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_201408940_sm_miscellaneous_information.pdf4 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
- 1aA. J. Esswein, D. G. Nocera, Chem. Rev. 2007, 107, 4022–4047;
- 1bJ. L. Dempsey, B. S. Brunschwig, J. R. Winkler, H. B. Gray, Acc. Chem. Res. 2009, 42, 1995–2004;
- 1cW. T. Eckenhoff, R. Eisenberg, Dalton Trans. 2012, 41, 13004–13021;
- 1dD. M. Schultz, T. P. Yoon, Science 2014, 343, 1239176.
- 2
- 2aK. M.-C. Wong, V. W.-W. Yam, Acc. Chem. Res. 2011, 44, 424–434;
- 2bE. Baggaley, J. A. Weinstein, J. A. G. Williams, Coord. Chem. Rev. 2012, 256, 1762–1785;
- 2cM. Mauro, A. Aliprandi, D. Septiadi, N. S. Kehr, L. De Cola, Chem. Soc. Rev. 2014, 43, 4144–4166.
- 3
- 3aS.-W. Lai, C.-M. Che, Top. Curr. Chem. 2004, 241, 27–63;
- 3bP. I. Djurovich, M. E. Thompson in Highly Efficient OLEDs with Phosphorescent Materials (Ed.: ), Wiley-VCH, Weinheim, 2008, pp. 131–161;
- 3cH. Yersin, A. F. Rausch, R. Czerwieniec, T. Hofbeck, T. Fischer, Coord. Chem. Rev. 2011, 255, 2622–2652;
- 3dP.-T. Chou, Y. Chi, M.-W. Chung, C.-C. Lin, Coord. Chem. Rev. 2011, 255, 2653–2665;
- 3eL. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido, Adv. Mater. 2011, 23, 926–952.
- 4
- 4aY. Kawamura, K. Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett. 2005, 86, 071104;
- 4bT. Sajoto, P. I. Djurovich, A. B. Tamayo, J. Oxgaard, W. A. Goddard III, M. E. Thompson, J. Am. Chem. Soc. 2009, 131, 9813–9822.
- 5
- 5aG. Cheng, P.-K. Chow, S. C. F. Kui, C.-C. Kwok, C.-M. Che, Adv. Mater. 2013, 25, 6765–6770;
- 5bE. Turner, N. Bakken, J. Li, Inorg. Chem. 2013, 52, 7344–7351.
- 6
- 6aJ. A. G. Williams, Chem. Soc. Rev. 2009, 38, 1783–1801;
- 6bA. F. Rausch, L. Murphy, J. A. G. Williams, H. Yersin, Inorg. Chem. 2012, 51, 312–319;
- 6cE. Rossi, A. Colombo, C. Dragonetti, D. Roberto, R. Ugo, A. Valore, L. Falciola, P. Brulatti, M. Cocchi, J. A. G. Williams, J. Mater. Chem. 2012, 22, 10650–10655;
- 6dP.-K. Chow, W.-P. To, K.-H. Low, C.-M. Che, Chem. Asian J. 2014, 9, 534–545;
- 6eA. M. Prokhorov, T. Hofbeck, R. Czerwieniec, A. F. Suleymanova, D. N. Kozhevnikov, H. Yersin, J. Am. Chem. Soc. 2014, 136, 9637–9642.
- 7
- 7aD. A. K. Vezzu, J. C. Deaton, J. S. Jones, L. Bartolotti, C. F. Harris, A. P. Marchetti, M. Kondakova, R. D. Pike, S. Huo, Inorg. Chem. 2010, 49, 5107–5119;
- 7bX.-C. Hang, T. Fleetham, E. Turner, J. Brooks, J. Li, Angew. Chem. Int. Ed. 2013, 52, 6753–6756; Angew. Chem. 2013, 125, 6885–6888.
- 8
- 8aW. Lu, B.-X. Mi, M. C. W. Chan, Z. Hui, C.-M. Che, N. Zhu, S.-T. Lee, J. Am. Chem. Soc. 2004, 126, 4958–4971;
- 8bS. C. F. Kui, I. H. T. Sham, C. C. C. Cheung, C.-W. Ma, B. Yan, N. Zhu, C.-M. Che, W.-F. Fu, Chem. Eur. J. 2007, 13, 417–435;
- 8cM. L. Clark, S. Diring, P. Retailleau, D. R. McMillin, R. Ziessel, Chem. Eur. J. 2008, 14, 7168–7179;
- 8dJ. Schneider, P. Du, P. Jarosz, T. Lazarides, X. Wang, W. W. Brennessel, R. Eisenberg, Inorg. Chem. 2009, 48, 4306–4316;
- 8eM.-Y. Yuen, S. C. F. Kui, K.-H. Low, C.-C. Kwok, S. S.-Y. Chui, C.-W. Ma, N. Zhu, C.-M. Che, Chem. Eur. J. 2010, 16, 14131–14141.
- 9
- 9aJ. D. Nguyen, E. M. D′Amato, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem. 2012, 4, 854–859;
- 9bH. Kim, C. Lee, Angew. Chem. Int. Ed. 2012, 51, 12303–12306; Angew. Chem. 2012, 124, 12469–12472.
- 10E. Shikhova, E. O. Danilov, S. Kinayyigit, I. E. Pomestchenko, A. D. Tregubov, F. Camerel, P. Retailleau, R. Ziessel, F. N. Castellano, Inorg. Chem. 2007, 46, 3038–3048.
- 11G. Revol, T. McCallum, M. Morin, F. Gagosz, L. Barriault, Angew. Chem. Int. Ed. 2013, 52, 13342–13345; Angew. Chem. 2013, 125, 13584–13587.
- 12C.-L. Ho, H. Li, W.-Y. Wong, J. Organomet. Chem. 2014, 751, 261–285.
- 13S.-H. Wu, C.-Y. Mou, H.-P. Lin, Chem. Soc. Rev. 2013, 42, 3862–3875.
- 14I. Slowing, B. G. Trewyn, V. S.-Y. Lin, J. Am. Chem. Soc. 2006, 128, 14792–14793.
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.