A class of fascinating optoelectronic materials: Triarylboron compounds

Science China Chemistry

Volumn 53, Issue 6, 2010, Pages 1235-1245

  Mou, Xin ^a   Liu, Shujuan ^a   Dai, Chunlei ^a   Ma, Tingchun ^a   Zhao, Qiang ^a,b   Ling, Qidan ^a   Huang, Wei ^a  

^a NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

OLEDs; optical properties; sensors; structure property relationships; triarylboron compounds

Indexed keywords

CHEMO-SENSORS; CYANIDE ION; ELECTRON TRANSPORT LAYERS; FLUORIDE ION; LEWIS ACID-BASE INTERACTION; OLEDS; OPTOELECTRONIC MATERIALS; STRUCTURAL CHARACTERISTICS; STRUCTURE PROPERTY RELATIONSHIPS;

CYANIDES; ELECTRON TRANSPORT PROPERTIES; IONS; LIGHT EMITTING DIODES; OPTOELECTRONIC DEVICES; ORGANIC LIGHT EMITTING DIODES (OLED); SENSORS; TRANSPORT PROPERTIES;

OPTICAL PROPERTIES;

EID: 77955505908     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-3190-1     Document Type: Article

References (58)

1. C.D. Entwistle T.B. Marder 2004 Applications of three-coordinate organoboron compounds and polymers in optoelectronics Chem Mater 16 23 4574 4585 10.1021/cm0495717 1:CAS:528:DC%2BD2cXls1ektL0%3D
2. Q. Zhao H. Y. Zhang A. Wakamiya S. Yamaguchi 2009 Coordination-induced intramolecular double cyclization: synthesis of boron-bridged dipyridylvinylenes and dithiazolylvinylenes Synthesis 1 127 132
3. M. Elbing G.C. Bazan 2008 A new design strategy for organic optoelectronic materials by lateral boryl substitution Angew Chem Int Ed 47 5 834 838 10.1002/anie.200703722 1:CAS:528:DC%2BD1cXhsV2nt74%3D (Pubitemid 351160272)
4. N. Matsumi Y. Chujo 2008 π-Conjugated organoboron polymers via the vacant p-orbital of the boron atom Polymer J 40 2 77 89 10.1295/polymj.PJ2007170 1:CAS:528:DC%2BD1cXkslSisr8%3D (Pubitemid 351496159)
5. Z.M. Hudson S. Wang 2009 Impact of donor-acceptor geometry and metal chelation on photophysical properties and applications of triarylboranes Acc Chem Res 42 10 1584 1596 10.1021/ar900072u 1:CAS:528:DC%2BD1MXnslGqtbk%3D
6. Y. Cui F.H. Li Z.H. Lu S. Wang 2007 Three-coordinate organoboron with a B=N bond: substituent effects, luminescence/electroluminescence and reactions with fluoride Dalton Trans 25 2634 264 10.1039/b703366d (Pubitemid 350092053)
7. M.H. Lee T. Agou J. Kobayashi T. Kawashima F.P. Gabbai 2007 Fluoride ion complexation by a cationic borane in aqueous solution Chem Commun 11 1133 1135 10.1039/b616814k (Pubitemid 46393930)
8. Y. Sun N. Ross S.B. Zhao K. Huszarik W.L. Jia R.Y. Wang D. Macartney S. 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 24 7510 7512 10.1021/ja0725652 1:CAS:528:DC%2BD2sXlslGgsLk%3D (Pubitemid 46981911)
9. R. Martinez-Manez F. Sancenon 2003 Fluorogenic and chromogenic chemosensors and reagents for anions Chem Rev 103 11 4419 4476 10.1021/cr010421e 1:CAS:528:DC%2BD3sXosVCqtb0%3D
10. P.A. Gale 2006 Structural and molecular recognition studies with acyclic anion receptors Acc Chem Res 39 7 465 475 10.1021/ar040237q 1:CAS:528: DC%2BD28XkvFGlu74%3D
11. W. L. Jia X. D. Feng D. R. Bai Z. H. Lu S. Wang G. Vamvounis 2005 MeS2B(p-4,4′-biphenyl-NPh(1-naphthyl)): A multifunctional molecule for electroluminescent devices Chem Mater 17 1 164 170 10.1021/cm048617t 1:CAS:528:DC%2BD2cXhtValsbvO (Pubitemid 40096119)
12. M. Mazzeo V. Vitale S.F. Della M. Anni G. Barbarella L. Favaretto G. Sotgiu R. Cingolani G. Gigli 2005 Bright white organic light-emitting devices from a single active molecular material Adv Mater 17 1 34 39 10.1002/adma.200400670 1:CAS:528:DC%2BD2MXhtVGht7w%3D (Pubitemid 40178442)
13. S. L. Lin L.H. Chan R.H. Lee M.Y. Yen W.J. Kuo C.T. Chen R.J. Jeng 2008 Highly efficient carbazole-π-dimesitylborane bipolar fluorophores for nondoped blue organic light-emitting diodes Adv Mater 20 20 3947 3952 10.1002/adma.200801023 1:CAS:528:DC%2BD1cXhtlOjsrrI
14. 2R (Ar = mesityl, R = 7-azaindolyl- or 2,2′-dipyridylaminofunctionalized aryl or thienyl) for electroluminescent devices and supramolecular assembly Chem Eur J 10 4 994 1006 10.1002/chem.200305579 1:CAS:528:DC%2BD2cXhvVKrtLc%3D
15. T. Noda Y. Shirota 1998 5,5′-Bis(dimesitylboryl)-2,2′- bithiophene and 5,5''-bis(dimesitylboryl)-2,2′:5′,2''-terthiophene as a novel family of electron-transporting amorphous molecular materials J Am Chem Soc 120 37 9714 9715 10.1021/ja9817343 1:CAS:528:DyaK1cXlslaktr8%3D (Pubitemid 28452678)
16. Z.Q. Liu Q. Fang D. Wang D.X. Cao G. Xue W.T. Yu H. Lei 2003 Trivalent boron as an acceptor in donor-acceptor-type compounds for single- and two-photon excited fluorescence Chem Eur J 9 20 5074 5084 10.1002/chem.200304833 1:CAS:528:DC%2BD3sXos1Sjsrw%3D
17. Z.Q. Liu Q. Fang D. Wang G. Xue W.T. Yu Z.S. Shao M.H. Jiang 2002 Trivalent boron as acceptor in D-π-A chromophores: Synthesis, structure and fluorescence following single- and two-photon excitation Chem Commun 23 2900 2901 10.1039/b207210f
18. J.C. Doty B. Babb P.J. Grisdale M. Glogowski J.L.R. Williams 1972 J Organomet Chem 38 229 236 10.1016/S0022-328X(00)83321-5 1:CAS:528: DyaE38XkslCnsLY%3D
19. C.H. Zhao A. Wakamiya Y. Inukai S. Yamaguchi 2006 Highly emissive organic solids containing 2,5-diboryl-1,4-phenylene unit J Am Chem Soc 128 50 15934 15935 10.1021/ja0637550 1:CAS:528:DC%2BD28Xht1GjsLrK (Pubitemid 44936536)
20. A. Wakamiya K. Mori S. Yamaguchi 2007 3-Boryl-2,2′-bithiophene as a versatile core skeleton for full-color highly emissive organic solids Angew Chem Int Ed 46 23 4273 4276 10.1002/anie.200604935 1:CAS:528: DC%2BD2sXmslCktb0%3D (Pubitemid 47040819)
21. C.H. Zhao A. Wakamiya S. Yamaguchi 2007 Highly emissive poly(aryleneethynylene) s containing 2,5-diboryl-1,4-phenylene as a building unit Macromolecules 40 11 3898 3900 10.1021/ma0702997 1:CAS:528: DC%2BD2sXks1SisrY%3D (Pubitemid 46953829)
22. D. Reitzenstein C. Lambert 2009 Localized versus backbone fluorescence in N-p-(diarylboryl)phenyl-substituted 2,7-and 3,6-linked polycarbazoles Macromolecules 42 3 773 782 10.1021/ma802232r 1:CAS:528:DC%2BD1MXnvFCksA%3D%3D
23. 2+ based on a rhodamine derivative and its application in bioimaging Sci China Ser B-Chem 52 6 760 764 10.1007/s11426-009-0126-8 1:CAS:528:DC%2BD1MXmtVegtbs%3D
24. L. Tang J.K. Jin S. Zhang Y. Mao J.Z. Sun W.Z. Yuan H. Zhao H.P. Xu A.J. Qin B.Z. Tang 2009 Detection of the critical micelle concentration of cationic and anionic surfactants based on aggregation-induced emission property of hexaphenylsilole derivatives Sci China Ser B-Chem 52 6 755 759 10.1007/s11426-009-0119-7 1:CAS:528:DC%2BD1MXmtVegtbg%3D
25. Riggs BL. Bone and Mineral Research. The Netherlands: Elsevier, 1984. 366-367
26. Wiseman A, Handbook of Experimental Pharmacology. Berlin: Springer-Verlag, 1970. 48-52
27. Kirk KL. Biochemistry of the Halogens and Inorganic Halides. New York: Plenum Press, 1991. 58-59
28. G. Zhou M. Baumgarten K. Mullen 2008 Mesitylboron-substituted ladder-type pentaphenylenes: Charge-transfer, electronic communication, and sensing properties J Am Chem Soc 130 37 12477 12484 10.1021/ja803627x 1:CAS:528:DC%2BD1cXhtValu77P
29. X.Y. Liu D.R. Bai S. Wang 2006 Charge-transfer emission in nonplanar three-coordinate organoboron compounds for fluorescent sensing of fluoride Angew Chem Int Ed 45 33 5475 5478 10.1002/anie.200601286 1:CAS:528: DC%2BD28XptVGjsro%3D (Pubitemid 44384329)
30. D.R. Bai X.Y. Liu S. Wang 2007 Charge-transfer emission involving three-coordinate organoboron: V-shape versus U-shape and impact of the spacer on dual emission and fluorescent sensing Chem Eur J 13 20 5713 5723 10.1002/chem.200700364 1:CAS:528:DC%2BD2sXotVaktb4%3D (Pubitemid 47117394)
31. D.X. Cao Z.Q. Liu G.H. Zhang G.Z. Li 2009 The synthesis, photophysical properties and fluoride anion recognition of a novel branched organoboron compound Dyes Pigments 81 3 193 196 10.1016/j.dyepig.2008.10.009 1:CAS:528:DC%2BD1MXhtVSqt7o%3D
32. 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 24 5481 5484 10.1021/ol052323b 1:CAS:528:DC%2BD2MXhtFOisLbN (Pubitemid 41775161)
33. V. Arnendola M. Bonizzoni D. Estebangomez L. Fabbrizzi M. Licchelli F. Sancenon A. Taglietti 2006 Some guidelines for the design of anion receptors Coord Chem Rev 250 11-12 1451 1470 10.1016/j.ccr.2006.01.006
34. S. Sole F.P. Gabbai 2004 A bidentate borane as colorimetric fluoride ion sensor Chem Commun 11 1284 1285 10.1039/b403596h
35. M. Melaimi F.P. Gabbai 2005 A heteronuclear bidentate Lewis acid as a phosphorescent fluoride sensor J Am Chem Soc 127 27 9680 9681 10.1021/ja053058s 1:CAS:528:DC%2BD2MXltlars7g%3D (Pubitemid 40981521)
36. Dorsey CL, Jewula P, Hudnall TW, Hoefelmeyer JD, Taylor TJ, Honesty NR, Chiu CW, Schulte M, Gabbai FP. Fluoride ion complexation by a B2/Hg heteronuclear tridentate lewis acid. Dalton Trans, 2008, 4442-4450
37. C.W. Chiu F.P. Gabbai 2006 Fluoride ion capture from water with a cationic borane J Am Chem Soc 128 44 14248 14249 10.1021/ja0658463 1:CAS:528:DC%2BD28XhtVyntb3K (Pubitemid 44707721)
38. M.H. Lee F.P. Gabbai 2007 Synthesis and properties of a cationic bidentate lewis acid Inorg Chem 46 20 8132 8138 10.1021/ic700360a 1:CAS:528:DC%2BD2sXlvFKju7Y%3D
39. 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 39 11978 11986 10.1021/ja073793z 1:CAS:528:DC%2BD2sXhtVWis7nO (Pubitemid 47512026)
40. T.W. Hudnall Y.M. Kim M.W. Bebbington D. Bourissou F.P. Gabbai 2008 Fluoride ion chelation by a bidentate phosphonium/borane Lewis acid J Am Chem Soc 130 33 10890 10891 10.1021/ja804492y 1:CAS:528:DC%2BD1cXovFyns78%3D
41. Y. Kim F.P. Gabbai 2009 Cationic boranes for the complexation of fluoride ions in water below the 4 ppm maximum contaminant level J Am Chem Soc 131 9 3363 3369 10.1021/ja8091467 1:CAS:528:DC%2BD1MXhvVSns7k%3D
42. S.B. Zhao T. Mccormick S. Wang 2007 Ambient-temperature metal-to-ligand charge-transfer phosphorescence facilitated by triarylboron: Bnpa and its metal complexes Inorg Chem 46 26 10965 10967 10.1021/ic7021215 1:CAS:528: DC%2BD2sXhtlKru73I
43. Y. Sun S. 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 8 3755 3767 10.1021/ic9000335 1:CAS:528:DC%2BD1MXisFemt7c%3D
44. Z.M. Hudson S.B. Zhao R.Y. Wang S. Wang 2009 Switchable Ambienttemperature singlet-triplet dual emission in nonconjugated donor-acceptor triarylboron-Pt-II complexes Chem Eur J 15 25 6131 6137 10.1002/chem.200900641 1:CAS:528:DC%2BD1MXnt12ltbs%3D
45. P.T. Chou Y. Chi 2007 Phosphorescent dyes for organic light-emitting diodes Chem Eur J 13 2 380 395 10.1002/chem.200601272 1:CAS:528: DC%2BD2sXns1Krtg%3D%3D
46. V. V. Grushin 2004 Mixed phosphine-phosphine oxide ligands Chem Rev 104 3 1629 1662 10.1021/cr030026j 1:CAS:528:DC%2BD2cXhsVOisLY%3D
47. Q. Zhao L. Li F. Y. Li M. X. Yu Z. P. Liu T. Yi C. H. Huang 2008 Aggregation-induced phosphorescent emission (AIPE) of iridium(III) complexes Chem Commun 6 685 687 10.1039/b712416c (Pubitemid 351171416)
48. 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 20 9256 9264 10.1021/ic800500c 1:CAS:528:DC%2BD1cXhtFGjsLzF
49. Xu WJ, Liu SJ, Zhao XY, Sun S, Cheng S, Ma TC, Sun HB, Zhao Q, Huang W. Novel cationic iridium(III) complex containing both triarylboron and carbazole moieties as ratiometric fluoride probe utilizing the switchable triplet-singlet emission. Chem Eur J, in press
50. 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 20 3820 3826 10.1002/adma.200702667 1:CAS:528:DC%2BD1cXhtlOjsrzN
51. S.T. Lam N.A. Zhu V.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 20 9664 9670 10.1021/ic900803a 1:CAS:528:DC%2BD1MXhtFWqtLvF
52. X.D. Lou Z. Li J.G. Qin 2009 DDTC-Na-based colorimetric chemosensor for the sensing of cyanide in water Sci China Ser B-Chem 52 6 802 808 10.1007/s11426-009-0111-2 1:CAS:528:DC%2BD1MXmtVegu78%3D
53. J.O. Huh Y. Do M.H. Lee 2007 A BODIPY borane dyad for the selective complexation of cyanide ion Organometallics. 27 6 1022 1025 10.1021/om701237t
54. C.W. Chiu Y. Kim F.P. Gabbai 2009 Lewis acidity enhancement of triarylboranes via peripheral decoration with cationic groups J Am Chem Soc 131 1 60 61 10.1021/ja808572t 1:CAS:528:DC%2BD1cXhsFWnsL%2FJ
55. Y. Kim H. Zhao F.P. Gabbai 2009 Sulfonium boranes for the selective capture of cyanide ions in water Angew Chem Int Ed 48 27 4957 4960 10.1002/anie.200901275 1:CAS:528:DC%2BD1MXnvFWrurY%3D
56. C.R. Wade F.P. Gabbai 2010 Cyanide anion binding by a triarylborane at the outer rim of a cyclometalated ruthenium(II) cationic complex Inorg Chem 49 2 714 720 10.1021/ic9020349 1:CAS:528:DC%2BD1MXhsFCltr7I
57. S. Yamaguchi S. Akiyama K. Tamao 2000 Tri-9-anthrylborane and its derivatives: New boron-containing pi-electron systems with divergently extended pi-conjugation through boron J Am Chem Soc 122 26 6335 6336 10.1021/ja994522u 1:CAS:528:DC%2BD3cXjvFKqt7Y%3D (Pubitemid 30456885)
58. S. Yasuhiko K. Motoi N. Tetsuya O. Kenji O. Takahiro 2000 A novel class of emitting amorphous molecular materials as bipolar radical formants: 2-"4-[bis(4-methylphenyl)amino]phenyl"-5-(dimesitylboryl) thiophene and 2-(4-[bis(9,9-dimethylfluorenyl)amino]phenyl)-5-(dimesityl-borly)thiophene J Am Chem Soc 122 44 11021 11022 10.1021/ja0023332