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A Comparative Study on Phosphorescent Cycloplatinated Complexes Based on Tridentate C^N^N-Coordinating Ligands and Phenylethynyl or Phenyl Ligand
Received date: 2017-09-08
Revised date: 2017-10-12
Online published: 2017-10-16
Two series of platinum complexes, 1a～6a and 1b-6b, based on tridentate cyclometalating ligands 2-aryl-6-(1H- pyrazol-1-yl)pyridine [Ar＝phenyl (L1), 2,4-difluorophenyl (L2), 3,5-dimethylphenyl (L3), 3-methoxyphenyl (L4), 2-thienyl (L5), 2-benzothienyl (L6)], and phenylethynyl and phenyl ancillary ligand were synthesized and characterized. The X-ray crystal structures of 2b, 3b and 5b were determined, which revealed a twisted orientation of the phenyl ligand with respect to the coordination plane and a weaker Pt—C(phenyl) bond compared with the Pt—C(alkynyl) bond in 1a. Photophysical properties including electronic absorption and emission spectra were studied. Complexes 1a～6a based on the phenylethynyl ligand were strongly emissive, while 1b～3b based on the phenyl ligand were only weakly emissive. However, 4b～6b displayed lower but decent photoluminescent quantum yields than those of 4a～6a, which is explained by the localization of the excited states in the tridentate cyclometalating ligands. The higher quantum efficiencies displayed by the complexes 1a～6a may be attributed to the stronger and more rigid acetylide ligand.
Mroz Robert , Vezzu Dileep A. K. , Wallace Brian , Ravindranathan Deepak , Carroll Jeffrey , Pike Robert D. , Huo Shouquan . A Comparative Study on Phosphorescent Cycloplatinated Complexes Based on Tridentate C^N^N-Coordinating Ligands and Phenylethynyl or Phenyl Ligand[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 171 -182 . DOI: 10.6023/cjoc201709010
[1] (a) Ma, Y.-G.; Cheung, T.-C.; Che, C.-M.; Shen, J.-C. Thin Solid Films 1998, 333, 224.
(b) Evans, R. C.; Douglas, P.; Williams, J. A. G.; Rochester, D. L. J. Fluoresc. 2006, 16, 201.
(c) Thomas Ⅲ, S. W.; Venkatesan, K.; Muller, P.; Swager, T. M. J. Am. Chem. Soc. 2006, 128, 16641.
(d) P. K.-M.; Lai, S.-W.; Lu, W.; Zhu, N.; Che, C.-M. Eur. J. Inorg. Chem. 2003, 2749.
(e) Lanoë, P.-H.; Fillaut, J.-L.; Toupet, L.; Williams, J. A. G.; Bozec, H. L.; Guerchais, V. Chem. Commun. 2008, 4333.
(f) Wong, K.-H.; Chan, M. C.-W.; Che, C.-M. Chem.-Eur. J. 1999, 5, 2845.
(g) Koo, C.-K.; Ho, Y.-M.; Chow, C.-F.; Lam, M. H.-W.; Lau, T.-C.; Wong, W.-Y. Inorg. Chem. 2007, 46, 3603.
(h) Feng, K.; Zhang, R. Y.; Wu, L.-Z.; Tu, B.; Peng, M.-L.; Zhang, L.-P.; Zhao, D.; Tung, C.-H. J. Am. Chem. Soc. 2006, 128, 14685.
[2] (a) Siu, P. K.-M.; Ma, D.-L.; Che, C.-M. Chem. Commun. 2005, 1025.
(b) Botchway, S. W.; Charnley, M.; Haycock, J. W.; Parker, A. W.; Rochetser, D. L.; Weinstein, J. A.; Williams, J. A. G. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 16071.
(c) Ma, D.-L.; Che, C.-M.; Yan, S.-C. J. Am. Chem. Soc. 2009, 131, 1835.
(d) Wu, P.; Wong, E. L.-M.; Ma, D.-L.; Tong, G. S.-M.; Ng, K.-M.; Che, C.-M. Chem. Eur. J. 2009, 15, 3652.
(e) Wieczorek, B.; Lemcke, B.; Dijkstra, H. P.; Egmond, M. R.; Gebbink, R. J. M. K.; van Koten, G. Eur. J. Inorg. Chem. 2010, 1929.
[3] (a) Williams, J. A. G.; Develay, S. D.; Rochester, D. L.; Murhy, L. Coord. Chem. Rev. 2008, 252, 2596.
(b) Xiang, H.-F.; Lai, S.-W.; Lai, P. T.; Che, C.-M. In Highly Efficient OLEDs with Phosphorescent Materials, Ed.:Yersin, H., Wiley-VCH, Weiheim, 2008.
(c) Kalinowski, J.; Fattori, V.; Cocchi, M.; Williams, J. A. G. Coord. Chem. Rev. 2011, 255, 2401.
(d) Baggaley, E.; Weinstein, J. A.; Williams, J. A. G. Coord. Chem. Rev. 2012, 256, 1762.
(e) Yang, X.; Yao, C.; Zhou, G. Platinum Metals Rev. 2013, 57, 2.
[4] Huo, S.; Carroll, J.; Vezzu, D. A. K. Asian J. Org. Chem. 2015, 4, 1210.
[5] (a) Constable, E. C.; Henney, R. P. G.; Leese, T. A.; Tocher, D. A. J. Chem. Soc., Chem. Commun. 1990, 513.
[6] Lai, S.-W.; Chan, M. C. W.; Cheung, T.-C.; Peng, S.-M.; Che, C.-M. Inorg. Chem. 1999, 38, 4046.
[7] Lu, W.; Mi, B.-X.; Chan, M. C. W.; Hui, Z.; Che, C.-M.; Zhu, N.; Lee, S. T. J. Am. Chem. Soc. 2004, 126, 4958.
[8] (a) Cheung, T.-C.; Cheung, K.-K.; Peng, S.-M.; Che, C.-M. J. Chem. Soc, Chem., Dalton Trans. 1996, 1645.
(b) Neve, F.; Crispini, A. Campagna, S. Inorg. Chem. 1997, 36, 6150.
(c) Lai, S.-W.; Chan, M. C. W.; Cheung, T.-C.; Peng, S.-M.; Che, C.-M. Inorg. Chem. 1999, 38, 4046.
(d) Hofmann, A.; Dahlenburg, L.; van Eldik, R. Inorg. Chem. 2003, 42, 6528.
(e) Che, C.-M.; Fu, W.-F.; Lai, S.-W.; Hou, Y.-J.; Liu, Y.-L. Chem. Commun. 2003, 118.
(f) Lanoë, P.-H.; Fillaut, J.-L.; Toupet, L.; Williams, J. A. G.; Bozec, H. L.; Guerchais, V. Chem. Commun. 2008, 4333.
(g) Schneider, J.; Du, P.; Wang, X.; Brennessel, W. W.; Eisenberg, R. Inorg. Chem. 2009, 48, 1498.
(h) Schneider, J.; Du, P.; Jarosz, P.; Lazarides, T.; Wang, X.; Brennessel, W. W.; Eisenberg, R. Inorg. Chem. 2009, 48, 4306.
[9] (a) Kui, S. C. F.; Sham, I. H. T.; Cheung, C. C. C.; Ma, C.-W.; Yan, B.; Zhu, N.; Che, C.-M.; Fu, W.-F. Chem.-Eur. J. 2007, 13, 417.
(b) Tong, G. S.-M.; Che, C.-M. Chem.-Eur. J. 2009, 15, 7225.
(c) Yuen, M.-Y.; Kui, S. C. F.; Low, K.-H.; Kwok, C.-C.; Chui, S. S.-Y.; Ma, C.-W.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2010, 16, 14131.
(d) Chow, P.-K.; Cheng, G.; Tong, G. S. M.; To, W.-P.; Kwong, W.-L.; Low, K.-H.; Kwok, C.-C.; Ma, C.; Che, C.-M. Angew. Chem., Int. Ed. 2015, 54, 2084.
[10] (a) Ravindranathan, D.; Vezzu, D. A. K.; Bartolotti, L.; Boyle, P. D.; Huo, S. Inorg. Chem. 2010, 49, 8922.
(b) Harris, C. F.; Vezzu, D. A. K.; Bartolotti, L.; Boyle, P. D.; Huo, S. Inorg. Chem. 2013, 52, 11711.
[11] (a) Chan, C.-W.; Cheng, L.-K.; Che, C.-M. Coord. Chem. Rev. 1994, 132, 87.
(b) Yam, V. W.-W.; Wong, K. M.-C. Top. Curr. Chem. 2005, 257, 1.
(c) Castellano, F. N.; Pomestchenko, I. E.; Shikhova, E.; Hua, F.; Muro, M. L.; Rajapakse, N. Coord. Chem. Rev. 2006, 250, 1819.
(d) Wong, K. M.-C.; Yam, V. W.-W. Coord. Chem. Rev. 2007, 251, 2477.
[12] Sowinski, A. F.; Deaton, J. C.; Huo, S. US 6824895, 2004.
[13] Gong, D.; Liu, W.; Chen, T.; Chen, Z.-R.; Huang, K.-W. J. Mol. Catal. Chem. A:Chem. 2014, 395, 100.
[14] Harris, C. F.; Ravindrananthan, D.; Huo, S. Tetrahedron Lett. 2012, 53, 5389.
[15] Vila, C.; Hornillos, V.; Fañanás-Mastral, M.; Feringa, B. L. Org. Biomol. Chem. 2014, 12, 9321.
[16] Minghetti, G.; Cinellu, M. A.; Chelucci, G.; Gladiali, S.; Demartin, F.; Manassero, M. J. Organomet. Chem. 1986, 307, 107.
[17] Kober, E. M.; Caspar, J. V.; Lumpkin, R. S.; Meyer, T. J. J. Phys. Chem. 1986, 90, 3722.
[18] Lees, A. J. Comments Inorg. Chem. 1995, 17, 319.
[19] Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193.
[20] Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697.
[21] Williams, J. A. G.; Beeby, A.; Davies, E. S.; Weinstein, J. A.; Wilson, C. Inorg. Chem. 2003, 42, 8609.
[22] SAINT PLUS, Bruker Analytical X-ray Systems, Madison, WI, 2001.
[23] SADABS, Bruker Analytical X-ray Systems, Madison, WI, 2001.
[24] Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
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