Abstract
A number of transition-metal complexes have been reported to exhibit rich luminescence, usually originating from phosphorescence. Such luminescence properties of the triplet excited state with a large Stoke’s shift, long lifetime, high luminescence quantum yield as well as lower excitation energy, are envisaged to serve as an ideal candidate in the area of potential applications for chemosensors, dye-sensitized solar cells, flat panel displays, optics, new materials and biological sciences. Organic alkynes (poly-ynes), with extended or conjugatedπ-systems and rigid structure with linear geometry, have become a significant research area due to their novel electronic and physical properties and their potential applications in nanotechnology. Owing to the presence of unsaturated sp-hybridized carbon atoms, the alkynyl unit can serve as a versatile building block in the construction of alkynyl transition-metal complexes, not only throughσ-bonding but also viaπ-bonding interactions. By incorporation of linear alkynyl groups into luminescent transition-metal complexes, the alkynyl moiety with goodσ-donor,π-donor andπ-acceptor abilities is envisaged to tune or perturb the emission behaviors, including emission energy (color), intensity and lifetime by its role as an auxiliary ligand as well as to govern the emission origin from its direct involvement. This review summarizes recent efforts on the synthesis of luminescent rod-like alkynyl complexes with different classes of transition metals and details the effects of the introduction of alkynyl groups on the luminescence properties of the complexes.
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Abbreviations
- tBu2bpy:
-
4,4′-di-tert-butyl-2,2′-bipyridine
- Bpy:
-
2,2′-bipyridine
- Fc:
-
ferrocene
- Np:
-
naphthylene
- Me2bpy:
-
4,4′-dimethyl-2,2′-bipyridine
- (CF3)2bpy:
-
4,4′-bis(trifluoromethyl)-2,2′-bipyridine
- Phen:
-
1,10-phenanthroline
- Dppm:
-
bis(diphenylphosphino)methane
- Dppa:
-
N,N-bis(diphenylphosphino)amine
- HOMO:
-
highest occupied molecular orbital
- LUMO:
-
lowest unoccupied molecular orbital
References
Horváth O, Stevenson KL (eds) (1993) Charge transfer photochemistry of coordination compounds. VCH, New York
Balzani V, Scandola F (eds) (1991) Supramolecular photochemistry. Ellis Horwood, Chichester, UK
Kalyanasundaram K (1992) Photochemistry of polypyridine and porphyrin complexes. Academic press, London
Solomon EI, Lever ABP (eds) (1999) Inorganic electronic structure and spectroscopy, Vol. II. Wiley, New York
Hagfeldt A, Grätzel M (1995) Chem Rev 95:49
Bignozzi CA, Argazzi R, Kleverlaan CJ (2000) Chem Soc Rev 29:87
Xie PH, Hou YJ, Zhang BW, Cao Y, Wu F, Tian WJ, Shen JC (1999) J Chem Soc Dalton Trans 4217
Klein C, Nazeeruddin MK, Censo DD, Liska P, Grätzel M (2004) Inorg Chem 43:4216
Baldo MA, O’Brien DF, Thompson ME, Forrest SR (1999) Phys Rev B 60:14422
Baldo MA, Thompson ME, Forrest SR (2000) Nature 403:750
Welter S, Brunner K, Hofstraat JW, De Cola L (2003) Nature 421:54
Xin H, Li FY, Shi M, Bian ZQ, Huang CH (2003) J Am Chem Soc 125:7166
Chan SC, Chan MCW, Che CM, Wang Y, Cheung KK, Zhu N (2001) Chem Eur J 7:4180
Lu W, Mi BX, Chan MCW, Hui Z, Che CM, Zhu N, Lee ST (2004) J Am Chem Soc 126:4958
Tour JM (2000) Acc Chem Res 33:791
Kim J, Swagar TM (2001) Nature 411:1030
Martin RE, Diederich F (1999) Angew Chem Int Ed 38:1350
Marder SR, Sohn JE, Stucky GD (eds) (1991) Materials for nonlinear optics: chemical perspectives. ACS Symposium Series vol 455. American Chemical Society, Washington, DC
Bruce DW, O’Hare D (eds) (1992) Inorganic materials. Wiley, Chichester, U.K.
Long NJ (1995) Angew Chem Int Ed Engl 34:21
Humphrey MG, Powell CE (2004) Coord Chem Rev 248:725
Manna J, John KD, Hopkins MD (1995) Adv Organomet Chem 38:79
Long NJ, Williams CK (2003) Angew Chem Int Ed 42:2586
Beljonne D, Wittman HF, Köhler A, Graham S, Younus M, Lewis J, Raithby PR, Khan MS, Friend RH, Brédas JL (1996) J Chem Phys 105:3868
Paul F, Lapinte C (1998) Coord Chem Rev 178–180:431
Houlding VH, Miskowski VM (1991) Coord Chem Rev 111:145
McMillin DR, Moore JJ (2002) Coord Chem Rev 229:113
Mihan S, Sunkel K, Beck W (1999) Chem Eur J 5:745
Lang H, Kohler K, Blau S (1995) Coord Chem Rev 143:113
Nast R (1982) Coord Chem Rev 47:89
Yam VWW, Yu KL, Cheung KK (1999) J Chem Soc Dalton Trans 2913
Abu-Salah OM, Al-Ohaly ARA (1998) J Chem Soc Dalton Trans 2297
Szafert S, Gladysz JA (2003) Chem Rev 103:4175
Wrighton MS, Morse DL (1974) J Am Chem Soc 96:998
Fredericks SM, Luong JC, Wrighton MS (1979) J Am Chem Soc 101:7415
Caspar JV, Meyer TJ (1983) J Phys Chem 87:952
Reitz A, Dressick WJ, Demas JN (1986) J Am Chem Soc 108:5344
Tapolsky G, Duesing R, Meyer TJ (1990) Inorg Chem 29:2285
Lin R, Fu Y, Brock CP, Guarr TF (1992) Inorg Chem 31:4346
Koike K, Okoshi N, Hori H, Takeuchi K, Ishitani O, Tsubaki H, Clark IP, George MW, Johnson FPA, Turner JJ (2002) J Am Chem Soc 124:11448
Yam VWW, Lau VCY, Cheung KK (1995) Organometallics 14:2749
Yam VWW, Chong SHF, Cheung KK (1998) Chem Commun 2121
Yam VWW, Lo KKW, Wong KMC (1998) J Organomet Chem 578:3
Yam VWW (2001) Chem Commun 789
Yam VWW, Chong SHF, Ko CC, Cheung KK (2000) Organometallics 19:5092
Yam VWW, Wong KMC, Chong SHF, Lau VCY, Lam SCF, Zhang L, Cheung KK (2003) J Organomet Chem 670:205
Yam VWW, Lau VCY, Cheung KK (1996) Organometallics 15:1740
Chong SHF (2000) PhD Thesis, The University of Hong Kong
Yam VWW, Chu BWK, Cheung KK (1998) Chem Commun 2261
Yam VWW, Chu BWK, Ko CC, Cheung KK (2001) J Chem Soc Dalton Trans 1911
Yam VWW, Ko CC, Chu BWK, Zhu N (2003) J Chem Soc Dalton Trans 3914
Wong CY, Chan MCW, Zhu N, Che CM (2004) Organometallics 23:2263
Sacksteder L, Baralt E, DeGraff BA, Lukehart CM, Demas JN (1991) Inorg Chem 30:2468
Choi CL, Cheng YF, Yip C, Phillips DL, Yam VWW (2000) Organometallics 19:3192
Lewis J, Khan MS, Kakkar AK, Johnson BFG, Marder TB, Fyfe HB, Wittmann F, Friend RH, Dray AE (1992) J Organomet Chem 425:165
Laine RM (ed) (1992) Fyfe HB, Mlekuz M, Stringer G, Taylor NJ, Marder TB Inorganic and organometallic polymers with special properties. NATO ASI Series. Kluwer Acad Publ, Dordrecht, The Netherlands, p331
Wittmann HF, Friend RH, Khan MS, Lewis J (1994) J Chem Phys 101:2694
Chawdhury N, Köhler A, Friend RH, Younus M, Long NJ, Raithby PR, Lewis J (1998) Macromolecules 31:722
Lewis J, Long NJ, Raithby PR, Shields GP, Wong WY, Younus M (1997) J Chem Soc Dalton Trans 4283
Wong WY, Wong WK, Raithby PR (1998) J Chem Soc Dalton Trans 2761
Lewis J, Raithby PR, Wong WY (1998) J Organomet Chem 556:219
Younus M, Köhler A, Cron S, Chawdhury N, Al-Mandhary MRA, Khan MS, Lewis J, Long NJ, Friend RH, Raithby PR (1998) Angew Chem Int Ed 37:3036
Wilson JS, Köhler A, Friend RH, Al-Suti MK, Al-Mandhary MRA, Khan MS, Raithby PR (2000) J Chem Phys113:7627
Köhler A, Wilson JS, Friend RH, Al-Suti MK, Khan MS, Gerhard A, Bässler H (2002) J Chem Phys 116:9457
Furlani A, Licoccia S, Russo MV, Villa AC, Guastini C (1982) J Chem Soc Dalton Trans 2449
Furlani A, Licoccia S, Russo MV, Billa AC, Guastini C (1984) J Chem Soc Dalton Trans 2197
Casalboni M, Sarcinelli F, Pizzoferrato R, D’Amato R, Furlani A, Russo MV (2000) Chem Phys Lett 319:107
D’Amato R, Furlani A, Colapietro M, Portalone G, Casalboni M, Falconieri M, Russo MV (2001) J Orgomet Chem 627:13
Liu Y, Jiang S, Glusac K, Powell DH, Anderson DF, Schanze KS (2002) J Am Chem Soc 124:12412
Stahl J, Bohling JC, Bauer EB, Peters TB, Mohr W, Martín-Alvarez JM, Hampel F, Gladysz JA (2002) Angew Chem Int Ed 41:1871
Mohr W, Stahl J, Hampel F, Gladysz JA (2003) Chem Eur J 9:3324
Pringle PG, Shaw BL (1982) J Chem Soc Dalton Trans 581
Zipp AP (1988) Coord Chem Rev 84:47
Smith DC, Gray HB (1990) Coord Chem Rev 100:169
Roundhill DM, Gray HB, Che CM (1989) Acc Chem Res 22:55
Yersin H, Humbs W, Strasser J (1997) Coord Chem Rev 159:325
Balch AL (1976) J Am Chem Soc 98:8049
Lewis NS, Mann KR, Gordon JG, Gray HB (1976) J Am Chem Soc 98:7461
Yam VWW, Yu KL, Wong KMC, Cheung KK (2000) Organometallics 20:721
Wong KMC, Hui CK, Yu KL, Yam VWW (2002) Coord Chem Rev 229:123
Yam VWW, Hui CK, Wong KMC, Zhu N, Cheung KK (2002) Organometallics 21:4326
Hui CK, Chu BWK, Zhu N, Yam VWW (2003) Inorg Chem 41:6178
Aldridge TK, Stacy EM, McMilin DR (1994) Inorg Chem 33:722
Bailey JA, Hill MG, Marsh RE, Miskowski VM, Schaefer WP, Gray HB (1995) Inorg Chem 34:4591
Büchner R, Cunningham CT, Field JS, Haines R, McMillin DR, Summerton GC (1999) J Chem Soc Dalton Trans 711
Büchner R, Field JS, Haines R, Cunningham CT, McMillin DR (1997) Inorg Chem 36:3952
Yip HK, Cheng LK, Cheung KK, Che CM (1993) J Chem Soc Dalton Trans 2933
Bailey JA, Miskowski VM, Gray HB (1993) Inorg Chem 32:369
Hill MG, Bailey JA, Miskowski VM, Gray HB (1996) Inorg Chem 35:4585
Arena G, Calogero G, Campagna S, Scolaro LM, Ricevuto V, Romeo R (1998) Inorg Chem 37:2763
Lai SW, Chan MCW, Cheung KK, Che CM (1999) Inorg Chem 38:4262
Yutaka T, Mori I, Kurihara M, Mizutani J, Tamai N, Kawai T, Irie M, Ishihara H (2002) Inorg Chem 41:7143
Yam VWW, Tang RPL, Wong KMC, Cheung KK (2001) Organometallics 20:4476
Yam VWW, Wong KMC, Zhu N (2003) Angew Chem Int Ed 42:1400
Yam VWW, Wong KMC, Zhu N (2002) J Am Chem Soc 12:6506
Wong KMC, Tang WS, Chu BWK, Zhu N, Yam VWW (2004) Organometallics 23:3459
Tzeng BC, Fu WF, Che CM, Chao HY, Cheung KK, Peng SM, (1999) J Chem Soc Dalton Trans 1017
Yam VWW, Tang RPL, Wong KMC, Ko CC, Cheung KK (2001) Inorg Chem 40:571
Osborn RS, Rogers D (1974) J Chem Soc Dalton Trans 1002
Herber RH, Croft M, Coyer MJ, Bilash B, Sahiner A (1994) Inorg Chem 33:2422
Yam VWW, Hui CK, Yu SY, Zhu N (2004) Inorg Chem 43:812
Lu W, Mi BX, Chan MCW, Hui Z, Zhu N, Lee ST, Che CM (2002) Chem Commun 206
Gamasa MP, Gimeno J, Lastra E, Aguirre A, Garcia-Granda (1989) J Organomet Chem 378:C11
Diéz J, Gamasa MP, Gimeno J, Aguirre A, Garcia-Granda (1991) Organometallics 10:380
Yam VWW, Lee WK, Lai TF (1993) Organometallics 12:2383
Yam VWW, Lee WK, Yeung PKY, Phillips D (1994) J Phys Chem 98:7545
Yam VWW, Fung WKM, Wong MT (1997) Organometallics 16:1772
Yam VWW, Fung WKM, Cheung KK (1998) Organometallics 17:3293
Yam VWW, Fung WKM, Cheung KK (1999) J Cluster Sci 10:37
Yam VWW (1997) J Photochem Photobiol A Chem 106:75
Yam VWW, Lo KKW, Fung WKM, Wang CR (1998) Coord Chem Rev 171:17
Lo WY, Lam CH, Yam VWW, Zhu N, Cheung KK, Fathallah S, Messaoudi S, Guennic BL, Kahlal S, Halet JF (2004) J Am Chem Soc 126:7300
Yam VWW, Fung WKM, Cheung KK (1997) Chem Commun 963
Yam VWW, Fung WKM, Cheung KK (1997) Organometallics 16:2032
Moore CE (1971) Natl Stand Ref Data Ser, US Natl Bur Stand, NSRDS-NBS 35:51&116
King C, Wang JC, Khan Md NI, Fackler JP (1989) Inorg Chem 28:2145
Che CM, Kwong HL, Yam VWW, Cho KC (1989) J Chem Soc Dalton Trans 885
Li D, Che CM, Kwong HL, Yam VWW (1992) J Chem Soc Dalton Trans 3325
Yam VWW, Lee WK (1993) J Chem Soc Dalton Trans 2097
Leung KH, Phillips DL, Tse MC, Che CM, Miskowski VM (1999) J Am Chem Soc 121:4799
Vogler A, Kunkely H (1988) Chem Phys Lett 150:135
Forward JM, Bohmann D, Fackler JP, Staples RJ (1995) Inorg Chem 34:6330
Mansour MA, Connick WB, Lachicotte RJ, Gysling HJ, Eisenberg R (1998) J Am Chem Soc 120:1329
Bickery JC, Olmstead MM, Fung EY, Balch AL (1997) Angew Chem Int Ed 36:1179
Yam VWW, Li CK, Chan CL (1998) Angew Chem 37:2857
Lee YA, McGarrah JE, Lachicotte RJ, Eisenberg R (2002) J Am Chem Soc 124:10662
White-Morris RL, Olmstead MM, Balch AL (2003) J Am Chem Soc 125:1033
White-Morris RL, Olmstead MM, Jiang F, Tinti DS, Balch AL (2002) J Am Chem Soc 124:2327
Li D, Hong X, Che CM, Lo WC, Peng SM (1993) J Chem Soc Dalton Trans 2929
Che CM, Yip HK, Lo WC, Peng SM (1994) Polyhedron 13:887
Shieh SJ, Hong X, Peng SM, Che CM (1994) J Chem Soc Dalton Trans 3067
Lu W, Zhu N, Che CM (2003) J Am Chem Soc 125:16081
Che CM, Choa HY, Miskowski VM, Li Y, Cheung KK (2001) J Am Chem Soc 123:4985
Lu W, Xiang HF, Zhu N, Che CM (2002) Organometallics 21:2343
Chao HY, Lu W, Chan MCW, Che CM, Cheung KK, Zhu N (2002) J Am Chem Soc 124:14696
Müller TE, Choi SWK, Mingos DMP, Murphy D, Williams DJ, Yam VWW (1994) J Organomet Chem 484:209
Yam VWW, Choi SWK, Cheung KK (1996) Organometallics 15:1734
Yam VWW, Choi SWK, Cheung KK (1996) J Chem Soc Dalton Trans 4227
Hunks WJ, MacDonald MA, Jennings MC, Puddephatt RJ (2000) Organometallics 19:5063
Irwin MJ, Vittal JJ, Puddephatt RJ (1997) Organometallics 16:3541
Schermann G, Grösser T, Hampel F, Hirsch A (1997) Chem Eur J 3:1105
Dembinski R, Bartik T, Jaeger M, Gladysz JA (2000) 122:810
Xiao H, Cheung KK, Che CM (1996) J Chem Soc Dalton Trans 3699
Vicent J, Chicote MT, Abrisqueta MD, Falcón-Alvarez AF (2002) J Organomet Chem 663:40
Ferrer M, Rodríguez, Rossell O, Pina F, Lima JC, Mardia MF, Solans X (2003) J Organomet Chem 678:82
Yamanoto Y, Shiotsuka M, Okuno S, Onaka S (2004) Chem Lett 33:210
Yam VWW, Fung WKM, Wong KMC, Lau VCY, Cheung KK (1998) Chem Commun 777
Yam VWW, Lo WY, Lam CH, Fung WKM, Wong KMC, Lau VCY, Zhu N (2003) Coord Chem Rev 245:39
Wong KMC, Lam SCF, Ko CC, Zhu N, Yam VWW, Roué S, Lapinte C, Fathallah S, Costuas K, Kahlal S, Halet JF (2003) Inorg Chem 42:7086
Cheung KL, Yip SK, Yam VWW (2004) J Organomet Chem 689:4451
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Yam, V.WW., Wong, K.MC. (2005). Luminescent Molecular Rods — Transition-Metal Alkynyl Complexes. In: Molecular Wires and Electronics. Topics in Current Chemistry, vol 257. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136069
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DOI: https://doi.org/10.1007/b136069
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