A near-infrared phosphorescent probe for F- based on a cationic iridium(III) complex with triarylboron moieties

Science China Chemistry

Volumn 54, Issue 11, 2011, Pages 1750-1758

  Xu, Wenjuan ^a   Liu, Shujuan ^a   Zhao, Qiang ^a   Ma, Tingchun ^a   Sun, Shi ^a   Zhao, Xinyan ^a   Huang, Wei ^a  

^a NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

F sensor; iridium(III) complex; NIR infrared; phosphorescent; triarylboron

Indexed keywords

BACKGROUND EMISSIONS; BORON ATOM; CN-LIGAND; COMPLEX 1; EXCITED-STATE PROPERTIES; EXPERIMENTAL METHODS; IRIDIUM COMPLEX; IRIDIUM(III) COMPLEX; LONG WAVELENGTH; MOLECULAR ORBITAL CALCULATIONS; NEAR INFRARED; NIR-INFRARED; PHOSPHORESCENT; PHOSPHORESCENT EMISSION; QUENCHING OF EMISSION; QUINOXALINES; SELECTIVE BINDING; SIGNAL TO NOISE; TRIARYLBORON;

BORON; BORON COMPOUNDS; EXCITED STATES; INFRARED DEVICES; IRIDIUM; LIGANDS; LIGHT EMISSION; METAL COMPLEXES; MOLECULAR ORBITALS; PHOSPHORESCENCE; PROBES; SIGNAL TO NOISE RATIO;

IRIDIUM COMPOUNDS;

EID: 80755175850     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4359-y     Document Type: Article

References (48)

1. P.D. Beer P.A. Gale 2001 Anion recognition and sensing: The state of the art and future perspectives Angew Chem Int Ed 40 486 516 10.1002/1521- 3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P 1:CAS:528: DC%2BD3MXhsVSrurc%3D (Pubitemid 32144453)
2. R. Martinez-Manez F. Sancenon 2003 Fluorogenic and chromogenic chemosensors and reagents for anions Chem Rev 103 4419 4476 10.1021/cr010421e 1:CAS:528:DC%2BD3sXosVCqtb0%3D
3. K. Bowman-James 2005 Alfred Werner revisited: The coordination chemistry of anions Acc Chem Res 38 671 678 10.1021/ar040071t 1:CAS:528: DC%2BD2MXlsV2rtrk%3D (Pubitemid 41260521)
4. V. Amendola D. Esteban-Gómez L. Fabbrizzi M. Licchelli 2006 What anions do to N-H-containing receptors Acc Chem Res 39 343 353 10.1021/ar050195l 1:CAS:528:DC%2BD28XjvVGqsbk%3D
5. P.A. Gale 2006 Structural and molecular recognition studies with acyclic anion receptors Acc Chem Res 39 465 475 10.1021/ar040237q 1:CAS:528: DC%2BD28XkvFGlu74%3D
6. Cametti M, Rissanen K. Recognition and sensing of fluoride anion. Chem Commun, 2009: 2809-2829
7. M. Boiocchi L. Del Boca D.E. Gómez L. Fabbrizzi M. Licchelli E. Monzani 2004 Nature of urea-fluoride interaction: Incipient and definitive proton transfer J Am Chem Soc 126 16507 16514 10.1021/ja045936c 1:CAS:528:DC%2BD2cXhtVagtLvN (Pubitemid 40081950)
8. 6 to polyamide-based cryptands J Am Chem Soc 126 12272 12273 10.1021/ja046078n 1:CAS:528:DC%2BD2cXntlaltrg%3D (Pubitemid 39304903)
9. S.O. Kang D. Powell V.W. Day K. Bowman-James 2006 Trapped bifluoride Angew Chem Int Ed 45 1921 1925 10.1002/anie.200504066 1:CAS:528: DC%2BD28XjtVyjtL0%3D (Pubitemid 44105217)
10. Lee MH, Agou T, Kobayashi J, Kawashima T, Gabba FP. Fluoride ion complexation by a cationic borane in aqueous solution. Chem Commun, 2007: 1133-1135 (Pubitemid 46393930)
11. X.Y. Liu D.R. Bai S.N. Wang 2006 Charge-transfer emission in nonplanar three-coordinate organoboron compounds for fluorescent sensing of fluoride Angew Chem Int Ed 45 5475 5478 10.1002/anie.200601286 1:CAS:528:DC%2BD28XptVGjsro%3D (Pubitemid 44384329)
12. K. Parab K. Venkatasubbaiah F. Jäkle 2006 Luminescent triarylborane-functionalized polystyrene: Synthesis, photophysical characterization, and anion-binding studies J Am Chem Soc 128 12879 12885 10.1021/ja063302v 1:CAS:528:DC%2BD28XptlOlu7c%3D (Pubitemid 44527764)
13. Ros-Lis JV, Martínez-Máñez R, Sancenón M, Soto J, Rurack K, Weishoff H. Signalling mechanisms in anion-responsive push-pull chromophores: The hydrogen-bonding, deprotonation and anionexchange chemistry of functionalized azo dyes. Eur J Org Chem, 2007: 2449-2458
14. Gale PA, Garcia-Garrido SE, Garric J. Anion receptors based on organic frameworks: Highlights from 2005 and 2006. Chem Soc Rev, 2007
15. H. Miyaji W. Sato J.L. Sessler 2000 Naked-eye detection of anions in dichloromethane: Colorimetric anion sensors based on calix[4]pyrrole Angew Chem Int Ed 39 1777 1780 10.1002/(SICI)1521-3773(20000515)39:10<1777::AID- ANIE1777>3.0.CO;2-E 1:CAS:528:DC%2BD3cXjsF2itrk%3D (Pubitemid 30365755)
16. F.P. Schmidtchen M. Berger 1997 Artificial organic host molecules for anions Chem Rev 97 1609 1646 10.1021/cr9603845 1:CAS:528:DyaK2sXksFSisLc%3D (Pubitemid 127659607)
17. V. Arnendola M. Bonizzoni D. Esteban-Gomez L. Fabbrizzi M. Licchelli F. Sancenon A. Taglietti 2006 Some guidelines for the design of anion receptors Coordin Chem Rev 250 1451 1470 10.1016/j.ccr.2006.01.006
18. Lin ZH, Ou SJ, Duan CY, Zhang RG, Bai ZP. Naked-eye detection of fluoride ion in water: A remarkably selective easy-to-prepare test paper. Chem Commun, 2006: 624-626
19. M.A. Palacios R. Nishiyabu M. Marquez P. Anzenbacher 2007 Supramolecular chemistry approach to the design of a high-resolution sensor array for multianion detection in water J Am Chem Soc 129 7538 7544 10.1021/ja0704784 1:CAS:528:DC%2BD2sXlvVels7w%3D (Pubitemid 46981916)
20. A. Aydogan D.J. Coady S.K. Kim A. Akar C.W. Bielawski M. Marquez J.L. Sessler 2008 Poly(methyl methacrylate)s with pendant calixpyrroles and crown ethers: Polymeric extractants for Potassium halides Angew Chem Int Ed 47 9648 9652 10.1002/anie.200803970 1:CAS:528:DC%2BD1cXhsFamu7nJ
21. R. Hu J.A. Feng D.H. Hu S.Q. Wang S.Y. Li Y. Li G.Q. Yang 2010 A rapid aqueous fluoride ion sensor with dual output modes Angew Chem Int Ed 49 4915 4918 10.1002/anie.201000790 1:CAS:528:DC%2BC3cXosV2rs7k%3D
22. Y. Kubo M. Yamamoto M. Ikeda M. Takeuchi S. Shinkai S. Yamaguchi K. Tamao 2003 A colorimetric and ratiometric fluorescent chemosensor with three emission changes: Fluoride ion sensing by a triarylborane-porphyrin conjugate Angew Chem Int Ed 42 2036 2040 10.1002/anie.200250788 1:CAS:528:DC%2BD3sXkt1Smsr8%3D (Pubitemid 36604343)
23. Z.Q. Liu M. Shi F.Y. Li Q. Fang Z.H. Chen T. Yi C.H. Huang 2005 Highly selective two-photon chemosensors for fluoride derived from organic boranes Org Lett 7 5481 5484 10.1021/ol052323b 1:CAS:528:DC%2BD2MXhtFOisLbN (Pubitemid 41775161)
24. S. Yamaguchi S. Akiyama K. Tamao 2001 Colorimetric fluoride ion sensing by boron-containing pi-electron systems J Am Chem Soc 123 11372 11375 10.1021/ja015957w 1:CAS:528:DC%2BD3MXnslOhsb0%3D (Pubitemid 33070595)
25. G. Patonay M.D. Antoine 1991 Near-infrared fluorogenic labels-New approach to an old problem Anal Chem 63 A321 A326 10.1021/ac00006a001
26. J. Fabian H. Nakazumi M. Matsuoka 1992 Near-infrared absorbing dyes Chem Rev 92 1197 1226 10.1021/cr00014a003 1:CAS:528:DyaK38XlsFakt7k%3D
27. T.W. Hudnall F.P. Gabbai 2007 Ammonium boranes for the selective complexation of cyanide or fluoride ions in water J Am Chem Soc 129 11978 11986 10.1021/ja073793z 1:CAS:528:DC%2BD2sXhtVWis7nO (Pubitemid 47512026)
28. Y.M. You S.Y. Park 2008 A Phosphorescent Ir(III) complex for selective fluoride ion sensing with a high signal-to-noise ratio Adv Mater 20 3820 3826 10.1002/adma.200702667 1:CAS:528:DC%2BD1cXhtlOjsrzN
29. E. Sakuda A. Funahashi N. Kitamura 2006 Synthesis and spectroscopic properties of platinum(II) terpyridine complexes having an arylborane charge transfer unit Inorg Chem 45 10670 10677 10.1021/ic061435b 1:CAS:528: DC%2BD28Xht1Chsb7P
30. Q. Zhao F.Y. Li C.H. Huang 2010 Phosphorescent chemosensors based on heavy-metal complexes Chem Soc Rev 39 3007 3030 10.1039/b915340c 1:CAS:528:DC%2BC3cXptFygsrw%3D
31. 2+ based on a phosphorescent iridium(III) complex Organometallics 26 2077 2081 10.1021/om061031r 1:CAS:528:DC%2BD2sXisFGrurg%3D (Pubitemid 46650450)
32. 2+ based on a phosphorescent iridium(III) complex. Dalton Trans, 2008: 3836-3840
33. H.L. Chen Q. Zhao Y.B. Wu F.Y. Li H. Yang T. Yi C.H. Huang 2007 Selective phosphorescence chemosensor for homocysteine based on an iridium(III) complex Inorg Chem 46 11075 11081 10.1021/ic7010887 1:CAS:528:DC%2BD2sXhtlGqt7nE
34. Q. Zhao F.Y. Li S.J. Liu M.X. Yu Z.Q. Liu T. Yi C.H. Huang 2008 Highly selective phosphorescent chemosensor for fluoride based on an iridium(III) complex containing arylborane units Inorg Chem 47 9256 9264 10.1021/ic800500c 1:CAS:528:DC%2BD1cXhtFGjsLzF
35. W.J. Xu S.J. Liu X.Y. Zhao S. Sun S. Cheng T.C. Ma H.B. Sun Q. Zhao W. Huang 2010 Cationic iridium(III) complex containing both triarylboron and carbazole moieties as a ratiometric fluoride probe that utilizes a switchable triplet-singlet emission Chem Eur J 16 7125 7133 1:CAS:528:DC%2BC3cXotVertrw%3D
36. S.B. Zhao T. McCormick S. Wang 2007 Ambient-temperature metal-toligand charge-transfer phosphorescence facilitated by triarylboron: Bnpa and its metal complexes Inorg Chem 46 10965 10967 10.1021/ic7021215 1:CAS:528: DC%2BD2sXhtlKru73I
37. Y. Sun N. Ross S.B. Zhao K. Huszarik W.L. Jia R.Y. Wang D. Macartney S.N. Wang 2007 Enhancing electron accepting ability of triarylboron via pi-conjugation with 2,2′-bipy and metal chelation: 5,5′-Bis(BMes(2)) -2,2′-bipy and its metal complexes J Am Chem Soc 129 7510 7512 10.1021/ja0725652 1:CAS:528:DC%2BD2sXlslGgsLk%3D (Pubitemid 46981911)
38. S.T. Lam N.A.Y. Zhu V.W.W. Yam 2009 Synthesis and characterization of luminescent rhenium(I) tricarbonyl diimine complexes with a triarylboron moiety and the study of their fluoride ion-binding properties Inorg Chem 48 9664 9670 10.1021/ic900803a 1:CAS:528:DC%2BD1MXhtFWqtLvF
39. Y.L. Rao S.N. Wang 2009 Impact of constitutional isomers of (BMes(2)) phenylpyridine on structure, stability, phosphorescence, and lewis acidity of mononuclear and dinuclear Pt(II) complexes Inorg Chem 48 7698 7713 10.1021/ic9007069 1:CAS:528:DC%2BD1MXoslOit7w%3D
40. Z.M. Hudson S.B. Zhao R.Y. Wang S.N. Wang 2009 Switchable ambient-temperature singlet-triplet dual emission in nonconjugated donoracceptor triarylboron-Pt-II complexes Chem Eur J 15 6131 6137 10.1002/chem.200900641 1:CAS:528:DC%2BD1MXnt12ltbs%3D
41. Y. Sun S.N. Wang 2009 Conjugated triarylboryl donor-acceptor systems supported by 2,2′-Bipyridine: Metal chelation impact on intraligand charger transfer emission, electron accepting ability, and "turn-on" fluoride sensing Inorg Chem 48 3755 3767 10.1021/ic9000335 1:CAS:528: DC%2BD1MXisFemt7c%3D
42. Q. Zhao S.J. Liu M. Shi C.M. Wang M.X. Yu L. Li F.Y. Li T. Yi C.H. Huang 2006 Series of new cationic iridium(III) complexes with tunable emission wavelength and excited state properties: Structures, theoretical calculations, and photophysical and electrochemical properties Inorg Chem 45 6152 6160 10.1021/ic052034j 1:CAS:528:DC%2BD28Xms1Kntr4%3D
43. A. Endo K. Suzuki T. Yoshihara S. Tobita M. Yahiro C. Adachi 2008 Measurement of photoluminescence efficiency of Ir(III) phenylpyridine derivatives in solution and solid-state films Chem Phys Lett 460 155 157 10.1016/j.cplett.2008.05.064 1:CAS:528:DC%2BD1cXovVCmtL4%3D
44. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb JRC, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople. Gaussian 03, revision C.02. Gaussian, Inc.: Wallingford, CT. 2003
45. M. Nonoyama 1974 [Benzo[h]quinolin-10-yl-N]iridium(III) complexes Bull Chem Soc Jpn 47 767 768 10.1246/bcsj.47.767 1:CAS:528:DyaE2cXhtlemu7o%3D
46. Q. Zhao S.J. Liu S. Sun C.M. Wang H.B. Sun F.Y. Li Q.L. Fan W. Huang 2011 DFT/TDDFT investigation of the modulation of photochromic properties in an organoboron-based diarylethene by fluoride ions Chemphyschem 12 313 321 10.1002/cphc.201000591
47. R.F. Chen J. Yin S.L. Zhang Q.D. Ling W. Huang 2010 Theoretical studies of the structural, electronic, and optical properties of phosphafluorenes J Phys Chem A 114 3655 3667 10.1021/jp911624v 1:CAS:528:DC%2BC3cXht1KmsLs%3D
48. Connors KA. Binding Constants: The Measurement of Molecular Complex Stability Constants. New York: John Wiley and Sonsm 1987. 161