Luminescent dinuclear rhenium(I) complexes containing bridging 1,2-diazine ligands: Photophysical properties and application

Coordination Chemistry Reviews

Volumn 256, Issue 15-16, 2012, Pages 1621-1643

  Panigati, Monica ^a   Mauro, Matteo ^b   Donghi, Daniela ^a   Mercandelli, Pierluigi ^a   Mussini, Patrizia ^a   De Cola, Luisa ^b   D'Alfonso, Giuseppe ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aggregation induced emission; Luminescence; Multiple redox centres; OLEDs; Rhenium complexes; TDDFT

Indexed keywords

EID: 84861949442     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2012.03.006     Document Type: Review

References (164)

1. Stukfens D.J., Vlček A. Coord. Chem. Rev. 1998, 177:127.
2. Crosby A.G. Coord. Chem. Rev. 2001, 211:163.
3. Lees A.J. Coord. Chem. Rev. 1998, 177:3.
4. Wrighton M., Morse D.L. J. Am. Chem. Soc. 1974, 96:998.
5. Giordano P.J., Fredericks S.M., Wrighton M., Morse D.L. J. Am. Chem. Soc. 1978, 100:2257.
6. Luong J.C., Nadjo L., Wrighton M. J. Am. Chem. Soc. 1978, 100:5790.
7. Fredericks S.M., Luong J.C., Wrighton M. J. Am. Chem. Soc. 1979, 101:7415.
8. Giordano P.J., Wrighton M. J. Am. Chem. Soc. 1979, 101:2888.
9. Smothers W.K., Wrighton M. J. Am. Chem. Soc. 1983, 105:1067.
10. Caspar J.V., Meyer T.J. J. Phys. Chem. 1983, 87:952.
11. Caspar J.V., Westmoreland T.D., Allen G.H., Bradley P.G., Meyer T.J., Woodruff W.H. J. Am. Chem. Soc. 1984, 106:3492.
12. Caspar J.V., Sullivan C.B., Meyer T.J. Inorg. Chem. 1984, 23:2104.
13. Kalyanasundaram K. J. Chem. Soc., Faraday Trans. 1986, 2(82):2401.
14. Tsubaki H., Sekine A., Ohashi Y., Koike K., Takeda H., Ishitani O. J. Am. Chem. Soc. 2005, 127:15544.
15. Richter M.M. Chem. Rev. 2004, 101:3003.
16. Fernandez-Moreira V., Thorp-Greenwood F.L., Coogan M.P. Chem. Commun. 2010, 46:186.
17. Lo K.K.-W. Top. Organomet. Chem. 2010, 29:115.
18. Lo K.K.-W., Hui W.K., Chung C.K., Tsang K.H.-K., Ng D.C.-M., Cheung K.-K. Coord. Chem. Rev. 2005, 249:1434.
19. Beck D., Brewer J., Lee J., McGraw D., Demas J.N. Coord. Chem. Rev. 2007, 251:546.
20. James S., Maresca K.P., Babich J.W., Valliant J.F., Doering L., Zubieta J. Bioconjugate Chem. 2006, 17:590. For some recent papers, see:.
21. Lo K.K.-W., Tsang K.H.-K., Zhu N. Organometallics 2006, 25:3220.
22. Reece S.J., Seyedsayamdost M.R., Stubbe J., Nocera D.G. J. Am. Chem. Soc. 2006, 128:13654.
23. Lo K.K.-W., Hui W.-K., Chung C.-K., Tsang K.H.-K., Lee T.K.-M., Li C.-K., Lau J.S.-Y., Ng D.C.-M. Coord. Chem. Rev. 2006, 250:1724.
24. Lo K.K.-W., Tsang K.H.-K., Zhu N. Inorg. Chem. 2005, 44:6100.
25. Wei L., Babich J., Eckelman W.C., Zubieta J. Inorg. Chem. 2005, 44:2198.
26. Di Bilio A.J., Crane B.R., Wehbi W.A., Kiser C.N., Abu-Omar M.M., Carlos R.M., Richards J.H., Winkler J.R., Gray H.B. J. Am. Chem. Soc. 2001, 123:3181.
27. Hillard E.A., Jaouen G. Organometallics 2011, 30:20.
28. Li X., Zhang D., Chi H., Xiao G., Dong Y., Wu S., Su Z., Zhang Z., Lei P., Hu Z., Li W. Appl. Phys. Chem. 2010, 97:263303. For OLED devices see for instance:.
29. Ranjan S., Lin S.-Y., Hwang K.-C., Chi Y., Ching W.-L., Liu C.-S., Tao Y.-T., Chien C.-H., Peng S.-M., Lee G.-H. Inorg. Chem. 2003, 42:1248.
30. Li Y., Liu Y., Guo J., Wu F., Tian W., Li B., Wang Y. Synth. Met. 2001, 118:175.
31. Li X., Zhang D., Li W., Chu B., Han L., Zhu J., Su Z., Bi D., Wang D., Yang D., Chen Y. Appl. Phys. Lett. 2008, 92:83302.
32. Li J., Si Z., Liu C., Li C., Zhao F., Duan Y., Chen P., Liu S., Li B. Semicond. Sci. Technol. 2007, 22:553.
33. Qian L., Bera D., Holloway P.H. Appl. Phys. Lett. 2007, 90:103511. For polymer light emitting devices see for instance:.
34. Lü Y.-Y., Jü C.-C., Guo D., Deng Z.-B., Wang K.-Z. J. Phys. Chem. C 2007, 111:5211.
35. David G., Walsh P.J., Gordon K.C. Chem. Phys. Lett. 2004, 383:292.
36. Wang Y.P., Xie W.F., Li B., Li W.L. Chin. Chem. Lett. 2007, 18:1501.
37. Li B., Li M., Hong Z., Li W., Yu T., Wei H. Appl. Phys. Lett. 2004, 85:4786.
38. Wallin S., Davidsson J., Modin J., Hammarström L. J. Phys. Chem. A 2005, 109:4697.
39. McCusker J.K. Acc. Chem. Res. 2003, 36:876.
40. Záliš S., Consani C., El Nahhas A., Cannizzo A., Chergui M., Hartl F., Vlček A. Inorg. Chim. Acta 2011, 374:578.
41. El Nahhas A., Cannizzo A., van Mourik F., Blanco-Rodriguez A.M., Záliš S., Vlček A., Chergui M. J. Phys. Chem. A 2010, 114:6361.
42. Vlček A., Záliš S. Coord. Chem. Rev. 2007, 251:258.
43. Sacksteder L., Lee M., Demas J.N., DeGraff B.A. J. Am. Chem. Soc. 1993, 115:8230.
44. Wallace L., Rillema D.P. Inorg. Chem. 1993, 32:3836.
45. Villegas J.M., Stoyanov S.R., Huang W., Rillema D.P. Inorg. Chem. 2005, 44:2297.
46. Obara S., Itabashi M., Okuda F., Tamaki S., Tanabe Y., Ishii Y., Nozaki K., Haga M. Inorg. Chem. 2006, 45:8907.
47. Baková R., Chergui M., Daniel C., Vlček A., Záliš S. Coord. Chem. Rev. 2011, 255:975.
48. Juris A., Campagna S., Bidd S., Lehn J.-M., Ziessel R. Inorg. Chem. 1988, 27:4007.
49. Rajendran T., Manimaran B., Lee F.-Y., Lee G.-H., Peng S.-M., Wang C.M., Lu K.-L. Inorg. Chem. 2000, 39:2016.
50. Kumar A., Sun S.-S., Lees A.J. Top. Organomet. Chem. 2010, 29:1.
51. Rajendran T., Manimaran B., Liao R.-T., Lin R.-J., Thanasekaran P., Lee G.-H., Peng S.-M., Liu Y.-H., Chang I.-J., Rajagopal S., Lu K.-L. Inorg. Chem. 2003, 42:6388.
52. Woessner S.M., Helms J.B., Shen Y., Sullivan B.P. Inorg. Chem. 1998, 37:5406.
53. Benkstein K.D., Hupp J.T., Stern C.L. Inorg. Chem. 1998, 37:5404.
54. Slone R.V., Benkstein K.D., Bélanger S., Hupp J.T., Guzei I.A., Rheingold A.L. Coord. Chem. Rev. 1998, 171:221.
55. Manimaran B., Thanasekaran P., Rajendran T., Lin R.-J., Chang I.-J., Lee G.-H., Peng S.-M., Rajagopal S., Lu K.-L. Inorg. Chem. 2002, 41:5323.
56. Tseng Y.-H., Bhattacharya D., Lin S.-M., Thanasekaran P., Wu J.-Y., Lee L.-W., Sathiyendiran M., Ho M.-L., Chung M.-W., Hsu K.-C., Chou P.-T., Lu K.-L. Inorg. Chem. 2010, 49:6805.
57. Abel E.W., Heard P.J., Orrell K.G. Inorg. Chim. Acta 1997, 255:65.
58. Chen Y., Shepherd R.E. Inorg. Chim. Acta 1998, 279:85.
59. Donghi D., D'Alfonso G., Mauro M., Panigati M., Mercandelli P., Sironi A., Mussini P., D'Alfonso L. Inorg. Chem. 2008, 47:4243.
60. Mauro M., Quartapelle Procopio E., Sun Y., Chien C.-H., Donghi D., Panigati M., Mercandelli P., Mussini P., D'Alfonso G., De Cola L. Adv. Funct. Mater. 2009, 19:2607.
61. Quartapelle Procopio E., Mauro M., Panigati M., Donghi D., Mercandelli P., Sironi A., D'Alfonso G., De Cola L. J. Am. Chem. Soc. 2010, 132:14397.
62. Panigati M., Donghi D., D'Alfonso G., Mercandelli P., Sironi A., D'Alfonso L. Inorg. Chem. 2006, 45:10909.
63. Raimondi A., Panigati M., Maggioni D., D'Alfonso L., Mercandelli P., Mussini P., D'Alfonso G. Inorg. Chem. 2012, 51:2966.
64. Sauer J., Heldmann D.K., Hetzenegger J., Krauthan J., Sichert H., Schuster J. Eur. J. Org. Chem. 1998, 2885.
65. Abel E.W., Blackwall E.S., Heard P.J., Orrel K.G., Sik V., Hursthouse M.B., Mazid A.M., Abdul Malik K.M. J. Chem. Soc., Dalton Trans. 1994, 100:445.
66. Lucenti E., D'Alfonso G., Macchi P., Maranesi M., Roberto D., Sironi A., Ugo R. J. Am. Chem. Soc. 2006, 128:12054. refs. therein.
67. Schmidt S.P., Nitschke J., Trogler W.C. Inorg. Synth. 1989, 26:113.
68. Ciani G., D'Alfonso G., Freni M., Romiti P., Sironi A. J. Organomet. Chem. 1978, 152:85.
69. Jiang C., Wen Y.-S., Liu L.-K., Hor T.S.A., Yan Y.K. Organometallics 1998, 17:173.
70. Herberhold M., Süss G., Ellermann J., Gäbelein H. Chem. Ber. 1978, 111:2931.
71. Saillant R., Barcelo G., Kaesz H. J. Am. Chem. Soc. 1970, 92:5739.
72. Wilson R.D., Bau R. J. Am. Chem. Soc. 1976, 98:4687.
73. Masciocchi N., D'Alfonso G., Kockelmann W., Schäfer W., Sironi A. Chem. Commun. 1997, 1903.
74. Beringhelli T., D'Alfonso G. J. Chem. Soc., Chem. Commun. 1994, 2631.
75. Beringhelli T., D'Alfonso G., Garavaglia M.G. J. Chem. Soc., Dalton Trans. 1996, 1771.
76. Wang S.R., Wang S.L., Cheng C.P., Yang C.S. J. Organomet. Chem. 1992, 431:215.
77. Beringhelli T., D'Alfonso G., Zarini M. J. Chem. Soc., Dalton Trans. 1995, 2407.
78. Wang S.R., Cheng C.P. J. Organomet. Chem. 1995, 490:111.
79. Shriver D.F., Kaesz H.D., Adams R.D. The Chemistry of Metal Cluster Complexes 1990, VCH, New York.
80. Masciocchi N., Sironi A., D'Alfonso G. J. Am. Chem. Soc. 1990, 112:9395.
81. D'Alfonso G. Chem. Eur. J. 2000, 6:209.
82. Beringhelli T., D'Alfonso G., Ciani G., Molinari H. J. Chem. Soc., Chem. Commun. 1987, 486.
83. Cotton F.A. Chemical Applications of Group Theory 1990, Wiley Interscience, New York. 3 ed.
84. Vega A., Calvo V., Manzur J., Spodine E., Saillard J.-Y. Inorg. Chem. 2002, 41:5382.
85. Tavazzi S., Silvestri L., Spearman P., Borghesi A., Mercandelli P., Panigati M., D'Alfonso G., Sironi A., De Cola L. Cryst. Growth Des. 2012, 12:742.
86. Zhang J., Frenking G. Chem. Phys. Lett. 2004, 394:120.
87. Wendt H., Bitterlich S. Electrochim. Acta 1992, 37:1951.
88. Said A.H., Mhalla F.M., Amatore C., Verpeaux J.N. J. Electroanal. Chem. 1999, 464:85.
89. Said A.H., Mhalla F.M., Amatore C., Thouin L., Pebay C., Verpeaux J.N. J. Electroanal. Chem. 2002, 537:39.
90. Saveant J.-M. Elements of Molecular and Biomolecular Electrochemistry. An Electrochemical Approach to Electron Transfer Chemistry 2006, Wiley, New York, p. 62.
91. Bard A.J., Faulkner L.R. Electrochemical Methods Fundamentals and Applications 2001, Wiley, New York.
92. Richter M.M., Debad J.D., Striplin D.R., Crosby G.A., Bard A.J. J. Am. Chem. Soc. 1996, 68:4370. refs. therein.
93. Graff J.L., Wrighton M.S. J. Am. Chem. Soc. 1981, 103:2225.
94. Vlček A. Top. Organomet. Chem. 2010, 29:73.
95. Halverson F., Hirt R.C. J. Phys. Chem. 1951, 19:711.
96. Hirt R.C., King F.T., Cavagnol J.C. J. Phys. Chem. 1956, 25:574.
97. Baba H., Goodman L., Valenti P.C. J. Am. Chem. Soc. 1966, 88:5410.
98. Worl L.A., Duesing R., Chen P., Della Ciana L., Meyer T.J. J. Chem. Soc., Dalton Trans. 1991, 849.
99. M. Mauro, Luminescent Re(I) and Ir(III) Complexes: From Design to Applications in Light-Emitting Devices, PhD Thesis, Milano, 2009, 72.
100. Förster Th., Kasper K.Z. Phys. Chem. 1954, 1:275.
101. Friend R.H., Gymer R.W., Holmes A.B., Burroughes J.H., Marks R.N., Taliani C., Bradley D.D.C., Dos Santos D.A., Brédas J.L., Lögdlund M., Salaneck W.R. Nature 1999, 397:121.
102. Kawamura Y., Brooks J., Brown J.J., Sasabe H., Adachi C. Phys. Rev. Lett. 2006, 96:017404.
103. Huang K., Wu H., Shi M., Li F., Yi T., Huang C. Chem. Commun. 2009, 1243.
104. Zhao Q., Li L., Li F., Yu M., Liu Z., Yi T., Huang C. Chem. Commun. 2008, 685.
105. Talarico A.M., Aiello I., Bellusci A., Crispini A., Ghedini M., Godbert N., Pugliese T., Szerb E. Dalton Trans. 2010, 39:1709.
106. Liu Y., Tao X., Wang F., Shi J., Sun J., Yu W., Ren Y., Zou D., Jiang M. J. Phys. Chem. C 2007, 111:6544.
107. Xiao S., Zou Y., Wu J., Zhou Y., Yi T., Li F., Huang C. J. Mater. Chem. 2007, 17:2483.
108. Tong H., Hong Y., Dong Y., Ren Y., Häussler M., Lam J.W.Y., Wong K.S., Tang B.Z. J. Phys. Chem. C 2007, 111:2287.
109. Kang H., Facchetti A., Jiang H., Cariati E., Righetto S., Ugo R., Zuccaccia C., Macchioni A., Stern C.L., Liu Z., Ho S.-T., Brown E.C., Ratner M.A., Marks T.J. J. Am. Chem. Soc. 2007, 129:3267.
110. Xie Z., Wang H., Li F., Xie W., Liu L., Yang B., Ye L., Ma Y. Cryst. Growth Des. 2007, 7:2512.
111. An B.-K., Kwon S.-K., Jung S.-D., Park S.Y. J. Am. Chem. Soc. 2002, 124:14410.
112. Luo J., Xie Z., Lam J.W.Y., Cheng L., Chen H., Qiu C., Kwok H.S., Zhan X., Liu Y., Zhu D., Tang B.Z. Chem. Commun. 2001, 1740.
113. Tang B.Z., Zhan X., Yu G., Lee P.P.S., Liu Y., Zhu D. J. Mater. Chem. 2001, 11:2974.
114. Zhao Z., Chen S., Shen X., Mahtab F., Yu Y., Lu P., Lam J.W.Y., Kwok H.S., Tang B.Z. Chem. Commun. 2010, 46:686.
115. Zhang G., Lu J., Sabat M., Fraser C.L. J. Am. Chem. Soc. 2010, 132:2160.
116. Tong H., Hong Y., Dong Y., Ren Y., Häussler M., Lam J.W.Y., Wong K.S., Tang B.Z. J. Phys. Chem. B 2007, 111:2000.
117. Sagara Y., Mutai T., Yoshikawa I., Araki K. J. Am. Chem. Soc. 2008, 129:1520.
118. Kim S., Zheng Q., He G.S., Bharali D.J., Pudavar H.E., Baev A., Prasad P.N. Adv. Funct. Mater. 2006, 16:2317.
119. Lee S.H., Jang B.-B., Kafafi Z.H. J. Am. Chem. Soc. 2005, 127:9071.
120. Hong Y., Lam J.W.Y., Tang B.Z. Chem. Commun. 2009, 4332.
121. Chen J., Xu B., Ouyang X., Tang B.Z., Cao Y. J. Phys. Chem. A 2004, 108:7522.
122. Zhu M.X., Lu W., Zhu N.Y., Che C.M. Chem. Eur. J. 2008, 14:9736.
123. Dong Y., Lam J.W.Y., Qin A., Sun J., Liu J., Li Z., Sun J., Sung H.H.-Y., Williams I.D., Kwok H.S., Tang B.Z. Chem. Commun. 2007, 177:3255.
124. Dong Y., Lam J.W.Y., Qin A., Li Z., Sun J., Sung H.H.-Y., Williams I.D., Tang B.Z. Chem. Commun. 2007, 177:40.
125. Shin C.H., Huh J.O., Lee M.H., Do Y. Dalton Trans. 2009, 6476.
126. Field J.S., Ledwaba L.P., Munro O.Q., McMillin D.R. CrystEngComm 2008, 10:740.
127. Yam V.W.W., Wong -K.M.-C., Zhu N. J. Am. Chem. Soc. 2002, 124:6506.
128. Brinkmann M., Gadret G., Muccini M., Taliani C., Masciocchi N., Sironi A. J. Am. Chem. Soc. 2000, 122:5147.
129. Fuan Y., Zhao Y., Ye L., Li B., Yang G., Wang Y. Cryst. Growth Des. 2009, 9:1421.
130. Campione M., Tavazzi S., Moret M., Porzio W. J. Appl. Phys. 2007, 101:083512.
131. Zhang H., Zhang Z., Ye K., Zhang J., Wang Y. Adv. Mater. 2006, 18:2369.
132. Davis R., Rath N.P., Das S. Chem. Commun. 2004, 74.
133. Pu Y.-J., Harding R.E., Stevenson S.G., Namdas E.B., Tedeschi C., Markham J.P.J., Rummings R.J., Burn P.L., Samuel I.D.W. J. Mater. Chem. 2007, 17:4255.
134. Thanasekaran P., Wu J.-Y., Manimaran B., Rajendran T., Chang I.-J., Rajagopal S., Lee G.-H., Peng S.-M., Lu K.-L. J. Phys. Chem. A 2007, 111:10953.
135. M. Mauro, C.-H. Yang, C.-Y. Shin, M. Panigati, C.-H. Chang, G. D'Alfonso, L. De Cola, Adv. Mater., in press. doi:10.1002/adma.201104831.
136. You Y., Park S.Y. Dalton Trans. 2009, 1267.
137. Yersin H. Highly Efficient OLEDs with Phosphorescent Materials 2008, Wiley-VCH, Weinheim, Germany.
138. Thompson M.E., Djurovich P.E., Barlow S., Marder S. Comprehensive Organometallic Chemistry III 2006, vol. 12:101. Elsevier, Oxford, UK.
139. Chi Y., Chou P.-T. Chem. Soc. Rev. 2010, 39:638.
140. Strassert C.A., Chien C.-H., Galvez Lopez M.D., Kourkoulos D., Hertel D., Meerholz K., De Cola L. Angew. Chem., Int. Ed. 2011, 50:946.
141. Kalinowski J., Fattori V., Cocchi M., Williams J.A.G. Coord. Chem. Rev. 2011, 225:2401.
142. Yersin H., Rausch A.F., Czerwieniec R., Hofbeck T., Fischer T. Coord. Chem. Rev. 2011, 255:2622.
143. Baldo M.A., Adachi C., Forrest S.R. Phys. Rev. B 2000, 62:10967.
144. Reineke S., Walzer K., Leo K. Phys. Rev. B 2007, 75:125328.
145. Zhou G.-J., Wong W.-Y., Yao B., Xie Z., Wang L. J. Mater. Chem. 2008, 18:1799.
146. Plummer E.A., van Dijken A., Hofstraat J.W., De Cola L., Brunner K. Adv. Funct. Mater. 2005, 15:281.
147. M. Mauro, M. Panigati, C.-H. Chang, G. D'Alfonso, L. De Cola, unpublished results.
148. Yam V.W.W., Wong K.M.C. Chem. Commun. 2011, 47:11579.
149. Balasingham R.G., Coogan M.P., Thorp-Greenwood F.L. Dalton. Trans. 2011, 40:11663.
150. Amoroso A.J., Coogan M.P., Dunne J.E., Fernández-Moreira V., Hess J.B., Hayes A.J., Lloyd D., Millet C., Pope S.J.A., Williams C. Chem. Commun. 2007, 3066.
151. Moore S.A., Frazier S.M., Sibbald M.S., DeGraff B.A., Demas J.N. Langmuir 2011, 27:9567.
152. Lo K.K.-W., Tsang K.H.K., Sze K.S., Chung C.K., Lee T.K.M., Zhang K.Y., Hui W.K., Li C.K., Lau J.S.Y., Ng D.C.M., Zhu N. Coord. Chem. Rev. 2007, 251:2292.
153. Ferri E., Donghi D., Panigati M., Prencipe G., D'Alfonso L., Zanoni I., Baldoli C., Maiorana S., D'Alfonso G., Licandro E. Chem. Commun. 2010, 46:6255.
154. Uhlmann E., Peyman A., Breipohl G., David W.W. Angew. Chem., Int. Ed. 1998, 37:2796.
155. Nielsen P.E. Peptide Nucleic Acids: Protocols and Applications 2004, Horizon Bioscience, Wymondham, UK. 2nd ed.
156. Simmons C.G., Pitts A.E., Mayfield L.D., Shay J.W., Corey D.R. Bioorg. Med. Chem. Lett. 1997, 7:3001.
157. Boffa L.C., Scarfi S., Mariani M.R., Damonte G., Allfrey V.G., Benati U., Morris P.L. Cancer Res. 2000, 60:2258.
158. Zhang X., Simmons C.G., Corey D.R. Bioorg. Med. Chem. Lett. 2001, 11:1269.
159. Hamilton S.E., Simmons C.G., Kathariya I., Corey D.R. Chem. Biol. 1999, 6:343.
160. Hamzavi R., Happ T., Weitershaus K., Metzler-Nolte N. J. Organomet. Chem. 2004, 689:4745.
161. Xavier C., Pak J.-K., Santos I., Alberto R. J. Organomet. Chem. 2007, 692:1332.
162. Xavier C., Giannini C., Dall'Angelo S., Gano L., Maiorana S., Alberto R., Santos I. J. Biol. Inorg. Chem. 2008, 13:1345.
163. Patra M., Gasser G., Bobukhov D., Merz K., Shtemenko A.V., Metzler-Nolte N. Dalton Trans. 2010, 39:5617.
164. Gurtovenko A.A., Anwar J. J. Phys. Chem. B 2007, 111:10453.