Volume 19, Issue 47 pp. 15924-15932

Full Paper

Cyclometalated Iridium(III) Complexes with Deoxyribose Substituents

Ayan Maity,

Ayan Maity

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Search for more papers by this author

Dr. Jung-Suk Choi,

Dr. Jung-Suk Choi

Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)

Search for more papers by this author

Dr. Thomas S. Teets,

Dr. Thomas S. Teets

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139 (USA)

Search for more papers by this author

Dr. Nihal Deligonul,

Dr. Nihal Deligonul

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Search for more papers by this author

Prof. Dr. Anthony J. Berdis,

Corresponding Author

Prof. Dr. Anthony J. Berdis

[email protected]

Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)

Anthony J. Berdis, Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)===

Thomas G. Gray, Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)===

Search for more papers by this author

Prof. Dr. Thomas G. Gray,

Corresponding Author

Prof. Dr. Thomas G. Gray

[email protected]

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Anthony J. Berdis, Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)===

Thomas G. Gray, Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)===

Search for more papers by this author

Ayan Maity,

Ayan Maity

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Search for more papers by this author

Dr. Jung-Suk Choi,

Dr. Jung-Suk Choi

Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)

Search for more papers by this author

Dr. Thomas S. Teets,

Dr. Thomas S. Teets

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139 (USA)

Search for more papers by this author

Dr. Nihal Deligonul,

Dr. Nihal Deligonul

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Search for more papers by this author

Prof. Dr. Anthony J. Berdis,

Corresponding Author

Prof. Dr. Anthony J. Berdis

[email protected]

Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)

Anthony J. Berdis, Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)===

Thomas G. Gray, Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)===

Search for more papers by this author

Prof. Dr. Thomas G. Gray,

Corresponding Author

Prof. Dr. Thomas G. Gray

[email protected]

Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)

Anthony J. Berdis, Department of Chemistry, Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115 (USA)===

Thomas G. Gray, Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA)===

Search for more papers by this author

First published: 08 October 2013

https://doi.org/10.1002/chem.201301776

Citations: 27

Share a link

Email
Facebook
x
LinkedIn
Reddit
Wechat
Bluesky

Graphical Abstract

Glow and tell: The study of enzymatic nucleoside transport suffers for lack of optical probes that can be tracked noninvasively. Presented here are nucleoside analogues in which emissive, cyclometalated iridium(III) complexes are “clicked” to C-1 of deoxyribose in place of canonical nucleobases (see picture). The resulting complexes show visible luminescence at room temperature and 77 K with microsecond-length triplet lifetimes.

Abstract

Fundamental study of enzymatic nucleoside transport suffers for lack of optical probes that can be tracked noninvasively. Nucleoside transporters are integral membrane glycoproteins that mediate the salvage of nucleosides and their passage across cell membranes. The substrate recognition site is the deoxyribose sugar, often with little distinction among nucleobases. Reported here are nucleoside analogues in which emissive, cyclometalated iridium(III) complexes are “clicked” to C-1 of deoxyribose in place of canonical nucleobases. The resulting complexes show visible luminescence at room temperature and 77 K with microsecond-length triplet lifetimes. A representative complex is crystallographically characterized. Transport and luminescence are demonstrated in cultured human carcinoma (KB3-1) cells.

Supporting Information

References

1Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 2013, 113, 192–270.
10.1021/cr2004103
CASPubMedWeb of Science®Google Scholar
2F. L. Thorp-Greenwood, Organometallics 2012, 31, 5686–5692.
10.1021/om3004477
CASWeb of Science®Google Scholar
3M. Patra, G. Gasser, ChemBioChem 2012, 13, 1232–1252.
10.1002/cbic.201200159
CASPubMedWeb of Science®Google Scholar
4E. Baggaley, J. A. Weinstein, J. A. G. Williams, Coord. Chem. Rev. 2012, 256, 1762–1785.
10.1016/j.ccr.2012.03.018
CASWeb of Science®Google Scholar
5F. L. Thorp-Greenwood, R. G. Balasingham, M. P. Coogan, J. Organomet. Chem. 2012, 714, 12–21.
10.1016/j.jorganchem.2012.01.020
CASWeb of Science®Google Scholar
6K. K.-W. Lo, A. W.-T. Choi, W. H.-T. Law, Dalton Trans. 2012, 41, 6021–6047.
10.1039/c2dt11892k
CASPubMedWeb of Science®Google Scholar
7K. K.-W. Lo, S. P.-Y. Li, K. Y. Zhang, New J. Chem. 2011, 35, 265–287.
10.1039/C0NJ00478B
CASWeb of Science®Google Scholar
8Q. Zhao, C. Huang, F. Li, Chem. Soc. Rev. 2011, 40, 2508–2524.
10.1039/c0cs00114g
CASPubMedWeb of Science®Google Scholar
9K. K.-W. Lo, K. Y. Zhang, S. P.-Y. Li, Pure Appl. Chem. 2011, 83, 823–840.
10.1351/PAC-CON-10-08-20
CASWeb of Science®Google Scholar
10K. L. Haas, K. J. Franz, Chem. Rev. 2009, 109, 4921–4960.
10.1021/cr900134a
CASPubMedWeb of Science®Google Scholar
11A. Ruggi, D. N. Reinhoudt, A. H. Velders, in Bioinorganic Medicinal Chemistry (Ed.: ), Wiley, New York 2011, pp. 383–406.
10.1002/9783527633104.ch13
Google Scholar
12S. Sprouse, K. A. King, P. J. Spellane, R. J. Watts, J. Am. Chem. Soc. 1984, 106, 6647–6653.
10.1021/ja00334a031
CASWeb of Science®Google Scholar
13K. A. King, P. J. Spellane, R. J. Watts, J. Am. Chem. Soc. 1985, 107, 1431–1432.
10.1021/ja00291a064
CASWeb of Science®Google Scholar
14Y. Ohsawa, S. Sprouse, K. A. King, M. K. DeArmond, K. W. Hanck, R. J. Watts, J. Phys. Chem. 1987, 91, 1047–1054.
10.1021/j100289a009
CASWeb of Science®Google Scholar
15K. Ichimura, T. Kobayashi, K. A. King, R. J. Watts, J. Phys. Chem. 1987, 91, 6104–6106.
10.1021/j100308a012
CASWeb of Science®Google Scholar
16F. O. Garces, K. A. King, R. J. Watts, Inorg. Chem. 1988, 27, 3464–3471.
10.1021/ic00293a008
CASWeb of Science®Google Scholar
17F. O. Garces, R. J. Watts, Inorg. Chem. 1990, 29, 582–584.
10.1021/ic00329a004
CASWeb of Science®Google Scholar
18K. Dedeian, P. I. Djurovich, F. O. Garces, G. Carlson, R. J. Watts, Inorg. Chem. 1991, 30, 1685–1687.
10.1021/ic00008a003
CASWeb of Science®Google Scholar
19A. P. Wilde, K. A. King, R. J. Watts, J. Phys. Chem. 1991, 95, 629–634.
10.1021/j100155a026
CASWeb of Science®Google Scholar
20C. Ulbricht, B. Beyer, C. Friebe, A. Winter, U. S. Schubert, Adv. Mater. 2009, 21, 4418–4441.
10.1002/adma.200803537
CASWeb of Science®Google Scholar
21H. Yersin, W. J. Finkenzeller, in Highly Efficient OLEDs with Phosphorescent Materials (Ed.: ), Wiley-VCH, Weinheim 2008, pp. 1–97.
Google Scholar
22F. Neve, A. Crispini, S. Campagna, S. Serroni, Inorg. Chem. 1999, 38, 2250–2258.
10.1021/ic981308i
CASWeb of Science®Google Scholar
23A. B. Tamayo, S. Garon, T. Sajoto, P. I. Djurovich, I. M. Tsyba, R. Bau, M. E. Thompson, Inorg. Chem. 2005, 44, 8723–8732.
10.1021/ic050970t
CASPubMedWeb of Science®Google Scholar
24S. Stagni, S. Colella, A. Palazzi, G. Valenti, S. Zacchini, F. Paolucci, M. Marcaccio, R. Q. Albuquerque, L. De Cola, Inorg. Chem. 2008, 47, 10509–10521.
10.1021/ic801157k
CASPubMedWeb of Science®Google Scholar
25A. F. Rausch, M. E. Thompson, H. Yersin, J. Phys. Chem. A 2009, 113, 5927–5932.
10.1021/jp902261c
CASPubMedWeb of Science®Google Scholar
26N. M. Shavaleev, F. Monti, R. D. Costa, R. Scopelliti, H. J. Bolink, E. Ortí, G. Accorsi, N. Armaroli, E. Baranoff, M. Grätzel, M. K. Nazeeruddin, Inorg. Chem. 2012, 51, 2263–2271.
10.1021/ic202297h
CASPubMedWeb of Science®Google Scholar
27N. M. Shavaleev, F. Monti, R. Scopelliti, A. Baschieri, L. Sambri, N. Armaroli, M. Grätzel, M. K. Nazeeruddin, Organometallics 2013, 32, 460–467.
10.1021/om300894m
CASWeb of Science®Google Scholar
28C. Li, M. Yu, Y. Sun, Y. Wu, C. Huang, F. Li, J. Am. Chem. Soc. 2011, 133, 11231–11239.
10.1021/ja202344c
CASPubMedWeb of Science®Google Scholar
29D.-L. Ma, W.-L. Wong, W.-H. Chung, F.-Y. Chan, P.-K. So, T.-S. Lai, Z.-Y. Zhou, Y.-C. Leung, K. Y. Wong, Angew. Chem. 2008, 120, 3795–3799;
10.1002/ange.200705319
Google Scholar
Angew. Chem. Int. Ed. 2008, 47, 3735–3739.
10.1002/anie.200705319
CASPubMedWeb of Science®Google Scholar
30X. Wang, J. Jia, Z. Huang, M. Zhou, H. Fei, Chem. Eur. J. 2011, 17, 8028–8032.
10.1002/chem.201100568
CASPubMedWeb of Science®Google Scholar
31Y. You, Y. Han, Y.-M. Lee, S. Y. Park, W. Nam, S. J. Lippard, J. Am. Chem. Soc. 2011, 133, 11488–11491.
10.1021/ja204997c
CASPubMedWeb of Science®Google Scholar
32Y. You, S. Lee, T. Kim, K. Ohkubo, W.-S. Chae, S. Fukuzumi, G.-J. Jhon, W. Nam, S. J. Lippard, J. Am. Chem. Soc. 2011, 133, 18328–18342.
10.1021/ja207163r
CASPubMedWeb of Science®Google Scholar
33P.-K. Lee, W. H.-T. Law, H.-W. Liu, K. K.-W. Lo, Inorg. Chem. 2011, 50, 8570–8579.
10.1021/ic201153d
CASPubMedWeb of Science®Google Scholar
34P. Steunenberg, A. Ruggi, N. S. van den Berg, T. Buckle, J. Kuil, F. W. B. van Leeuwen, A. H. Velders, Inorg. Chem. 2012, 51, 2105–2114.
10.1021/ic201860s
CASPubMedWeb of Science®Google Scholar
35Q. Zhao, M. Yu, L. Shi, S. Liu, C. Li, M. Shi, Z. Zhou, C. Huang, F. Li, Organometallics 2010, 29, 1085–1091.
10.1021/om900691r
CASWeb of Science®Google Scholar
36K. K.-W. Lo, J. S.-W. Chan, L.-H. Lui, C.-K. Chung, Organometallics 2004, 23, 3108–3116.
10.1021/om0499355
CASWeb of Science®Google Scholar
37K. K-W. Lo, J. S.-Y. Lau, Inorg. Chem. 2007, 46, 700–709.
10.1021/ic0612202
CASPubMedWeb of Science®Google Scholar
38K. K-W. Lo, K. Y. Zhang, S.-K. Leung, M.-C. Tang, Angew. Chem. 2008, 120, 2245–2248;
10.1002/ange.200705155
Web of Science®Google Scholar
Angew. Chem. Int. Ed. 2008, 47, 2213–2216.
10.1002/anie.200705155
CASPubMedWeb of Science®Google Scholar
39K. K.-W. Lo, K. Y. Zhang, C.-K. Chung, K. Y. Kwok, Chem. Eur. J. 2007, 13, 7110–7120.
10.1002/chem.200700530
CASPubMedWeb of Science®Google Scholar
40H.-W. Liu, K. Y. Zhang, W. H.-T. Law, K. K.-W. Lo, Organometallics 2010, 29, 3474–3476.
10.1021/om100597g
CASWeb of Science®Google Scholar
41J.-S. Choi, A. J. Berdis, Future Med. Chem. 2012, 4, 1461–1478.
10.4155/fmc.12.79
CASPubMedWeb of Science®Google Scholar
42K. M. Smith, M. D. Slugoski, S. K. Loewen, A. M. Ng, S. Y. Yao, X. Z. Chen, E. Karpinski, C. E. Cass, S. A. Baldwin, J. D. Young, J. Biol. Chem. 2005, 280, 25436–25449.
10.1074/jbc.M409454200
CASPubMedWeb of Science®Google Scholar
43A. J. Berdis, Biochemistry 2008, 47, 8253–8260.
10.1021/bi801179f
CASPubMedWeb of Science®Google Scholar
44W. Plunkett, V. Gandhi, Hematol. Cell Ther. 1996, 38 Suppl 2, S 67–74.
Google Scholar
45V. Gandhi, W. Plunkett, Clin. Pharmacokinet. 2002, 41, 93–103.
10.2165/00003088-200241020-00002
CASPubMedWeb of Science®Google Scholar
46W. B. Parker, J. A. Secrist 3rd, W. R. Waud, Curr. Opin. Investig. Drugs 2004, 5, 592–596.
CASPubMedGoogle Scholar
47V. Gandhi, W. Plunkett, Curr. Opin. Oncol. 2006, 18, 584–590.
10.1097/01.cco.0000245326.65152.af
CASPubMedWeb of Science®Google Scholar
48D. S. Gesto, N. M. F. S. A. Cerqueira, P. A. Fernandes, M. J. Ramos, Curr. Med. Chem. 2012, 19, 1076–1087.
10.2174/092986712799320682
CASPubMedWeb of Science®Google Scholar
49P. W. Marks, Expert Rev. Anticancer Ther. 2012, 12, 299–305.
10.1586/era.11.207
CASPubMedWeb of Science®Google Scholar
50C. A. Koczor, R. A. Torres, W. Lewis, Expert Opin. Drug Metab. Toxicol. 2012, 8, 665–676.
10.1517/17425255.2012.680885
CASWeb of Science®Google Scholar
51T. Robak, P. Robak, Curr. Pharm. Des. 2012, 18, 3373–3388.
10.2174/138161212801227005
CASPubMedWeb of Science®Google Scholar
52Z. L. Johnson, C.-G. Cheong, S.-Y. Lee, Nature 2012, 483, 489–493.
10.1038/nature10882
CASPubMedWeb of Science®Google Scholar
53For an alternative metalation, see: A. Maity, B. L. Anderson, N. Deligonul, T. G. Gray, Chem. Sci. 2013, 4, 1175–1181.
10.1039/c2sc21831c
CASWeb of Science®Google Scholar
54For examples of cyclometalated iridium(III) complexes bearing one chelating triazole or triazolate ligand, see:
Google Scholar
54aS. Liu, P. Müller, M. K. Takase, T. M. Swager, Inorg. Chem. 2011, 50, 7598–7609;
10.1021/ic2005985
CASPubMedWeb of Science®Google Scholar
54bS. Zanarini, M. Felici, G. Valenti, M. Marcaccio, L. Prodi, S. Bonacchi, P. Contreras-Carballada, R. M. Williams, M. C. Feiters, R. J. M. Nolte, L. De Cola, F. Paolucci, Chem. Eur. J. 2011, 17, 4640–4647;
10.1002/chem.201002956
CASPubMedWeb of Science®Google Scholar
54cB. Beyer, C. Ulbricht, D. Escudero, C. Friebe, A. Winter, L. González, U. S. Schubert, Organometallics 2009, 28, 5478–5488;
10.1021/om9003785
CASWeb of Science®Google Scholar
54dE. Orselli, R. Q. Albuquerque, P. M. Fransen, R. Fröhlich, H. M. Janssen, L. De Cola, J. Mater. Chem. 2008, 18, 4579–4590.
10.1039/b805324c
CASWeb of Science®Google Scholar
55J. M. Fernández-Hernández, J. I. Beltrán, V. Lemaur, M.-D. Gálvez-López, C.-H. Chien, F. Polo, E. Orselli, R. Fröhlich, J. Cornil, L. De Cola, Inorg. Chem. 2013, 52, 1812–1824.
10.1021/ic3018419
CASPubMedWeb of Science®Google Scholar
56K. N. Swanick, S. Ladouceur, E. Zysman-Colman, Z. Ding, Chem. Commun. 2012, 48, 3179–3181.
10.1039/c2cc16385c
CASPubMedWeb of Science®Google Scholar
57A. B. Tamayo, B. D. Alleyne, P. I. Djurovich, S. Lamansky, I. Tsyba, N. N. Ho, R. Bau, M. E. Thompson, J. Am. Chem. Soc. 2003, 125, 7377–7387.
10.1021/ja034537z
CASPubMedWeb of Science®Google Scholar
58Y. You, W. Nam, Chem. Soc. Rev. 2012, 41, 7061–7084.
10.1039/c2cs35171d
CASPubMedWeb of Science®Google Scholar
59R. S. Mulliken, J. Chem. Phys. 1955, 23, 1833–1840.
10.1063/1.1740588
CASWeb of Science®Google Scholar
60L. Dagnino, L. L. Bennett, Jr., A. R. P. Paterson, J. Biol. Chem. 1991, 266, 6312–6317.
10.1016/S0021-9258(18)38119-5
CASPubMedWeb of Science®Google Scholar
61M. M. Gutierrez, K. M. Giacomini, Biochim. Biophys. Acta 1993, 1149, 202–208.
10.1016/0005-2736(93)90202-B
CASPubMedWeb of Science®Google Scholar
62M. E. Schaner, J. Wang, L. Zhang, S.-F. Su, K. M. Gerstin, K. M. Giacomini, J. Pharmacol. Exp. Ther. 1999, 289, 1487–1491.
CASPubMedWeb of Science®Google Scholar
63K. M. King, V. L. Damaraju, M. F. Vickers, S. Y. Yao, T. Lang, T. E. Tackaberry, D. A. Mowles, A. M. Ng, J. D. Young, C. E. Cass, Mol. Pharmacol. 2006, 69, 346–353.
CASPubMedWeb of Science®Google Scholar
64A. N. Elwi, V. L. Damaraju, M. L. Kuzma, D. A. Mowles, S. A. Baldwin, J. D. Young, M. B. Sawyer, C. E. Cass, Am. J. Physiol. Renal Physiol. 2009, 296, F 1439–1451.
10.1152/ajprenal.90411.2008
CASPubMedWeb of Science®Google Scholar
65H. Li, G. A. Smolen, L. F. Beers, L. Xia, W. Gerald, J. Wang, D. A. Haber, S. B. Lee, PLoS One 2008, 3, e 2353.
10.1371/journal.pone.0002353
CASPubMedWeb of Science®Google Scholar
66D. A. Griffith, S. M. Jarvis, Biochim. Biophys. Acta 1996, 1286, 153–181.
10.1016/S0304-4157(96)00008-1
CASPubMedWeb of Science®Google Scholar
67M. Podgorska, K. Kocbuch, T. Pawelczyk, Acta Biochim. Pol. 2005, 52, 749–758.
CASPubMedWeb of Science®Google Scholar
68V. Rolland, M. Kotera, J. Lhomme, Synth. Commun. 1997, 27, 3505–3511.
10.1080/00397919708007071
CASWeb of Science®Google Scholar
69M. Nonoyama, Bull. Chem. Soc. Jpn. 1974, 47, 767–768.
10.1246/bcsj.47.767
CASWeb of Science®Google Scholar
70E. Baranoff, B. F. E. Curchod, J. Frey, R. Scopelliti, F. Kessler, I. Tavernelli, U. Rothlisberger, M. Graetzel, Md. K. Nazeeruddin, Inorg. Chem. 2012, 51, 215–224.
10.1021/ic202162q
CASPubMedWeb of Science®Google Scholar
71I. Shin, S. Yoon, J. I. Kim, J. Lee, T. H. Kim, H. Kim, Electrochim. Acta 2011, 56, 6219–6223.
10.1016/j.electacta.2011.03.075
CASWeb of Science®Google Scholar
72T. Peng, Y. Yang, Y. Liu, D. Ma, Z. Houc, Y. Wang, Chem. Commun. 2011, 47, 3150–3152.
10.1039/c0cc04684a
CASPubMedWeb of Science®Google Scholar
73M. Schmittel, S. Qinghai, Chem. Commun. 2012, 48, 2707–2709.
10.1039/c2cc17731e
CASPubMedWeb of Science®Google Scholar
74S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304–4312.
10.1021/ja003693s
CASPubMedWeb of Science®Google Scholar
75E. J. McLaurin, A. B. Greytak, M. G. Bawendi, D. G. Nocera, J. Am. Chem. Soc. 2009, 131, 12994–13001.
10.1021/ja902712b
CASPubMedWeb of Science®Google Scholar
76J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991–1024.
10.1021/j100678a001
CASWeb of Science®Google Scholar
77S. Hamai, F. Hirayama, J. Phys. Chem. 1983, 87, 83–89.
10.1021/j100224a020
CASWeb of Science®Google Scholar
78Bruker Advanced X-ray Solutions, SMART for WNT/2000 (Version 5.628), Bruker AXS, Inc., Madison, WI, 1997–2002.
Google Scholar
79Bruker Advanced X-ray Solutions, SAINT, Version 6.45, Bruker AXS, Inc., Madison, WI, 1997–2003.
Google Scholar
80Bruker Advanced X-ray Solutions, SHELXTL, Version 6.10, Bruker AXS, Inc., Madison, WI, 2000.
Google Scholar
81Gaussian 09 (Revision A.02), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
Google Scholar
82J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865–3868.
10.1103/PhysRevLett.77.3865
CASPubMedWeb of Science®Google Scholar
83S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117–129.
10.1016/0301-0104(81)85090-2
CASWeb of Science®Google Scholar
84J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999–3093.
10.1021/cr9904009
CASPubMedWeb of Science®Google Scholar
85E. Cancès, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032–3041.
10.1063/1.474659
CASWeb of Science®Google Scholar
86B. Mennucci, E. Cancès, J. Tomasi, J. Phys. Chem. B 1997, 101, 10506–10517.
10.1021/jp971959k
CASWeb of Science®Google Scholar
87S. I. Gorelsky, AOMix: Program for Molecular Orbital Analysis, York University, Toronto, 1997: http://www.sg-chem.net.
Google Scholar
88S. I. Gorelsky, A. B. P. Lever, J. Organomet. Chem. 2001, 635, 187–196.
10.1016/S0022-328X(01)01079-8
CASWeb of Science®Google Scholar

Citing Literature

Volume19, Issue47

November 18, 2013

Pages 15924-15932

Cyclometalated Iridium(III) Complexes with Deoxyribose Substituents

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Cyclometalated Iridium(III) Complexes with Deoxyribose Substituents

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Related

Information