Harvesting solar energy using conjugated metallopolyyne donors containing electron-rich phenothiazine-oligothiophene moieties

Journal of Organometallic Chemistry

Volumn 694, Issue 17, 2009, Pages 2717-2726

  Wong, Wai Yeung ^a   Chow, Wing Cheong ^a   Cheung, Kai Yin ^b   Fung, Man Kin ^b   Djurišić, Aleksandra B ^b   Chan, Wai Kin ^b  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Metallopolyynes; Oligothiophene; Phenothiazine; Photovoltaics; Platinum

Indexed keywords

ABSORPTION CAPABILITY; ABSORPTION WAVELENGTHS; AIR MASS; BLEND RATIOS; BULK HETEROJUNCTION; BUTYRIC ACIDS; DINUCLEAR MODEL; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTRON-RICH; EXTERNAL QUANTUM EFFICIENCY; FILL-FACTOR; FUNCTIONALIZED; LIGHT-HARVESTING; METALLOPOLYMERS; METALLOPOLYYNES; METHANOFULLERENE; METHYL ESTERS; OLIGOTHIOPHENE; ORGANOMETALLIC POLYMER; PHENOTHIAZINE; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOVOLTAIC PROPERTY; PHOTOVOLTAICS; POLYMER CHAINS; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; POWER DEPENDENCY; PROCESSABLE; SOLAR CELL EFFICIENCIES; SOLAR CELL PARAMETERS; SOLAR ILLUMINATION; SPECTRAL REGION; THIENYL RING;

ABSORPTION; BLENDING; CONVERSION EFFICIENCY; ELECTRON TRANSITIONS; ENERGY CONVERSION; ESTERS; FATTY ACIDS; HARVESTING; HETEROJUNCTIONS; INSECTICIDES; ORGANOMETALLICS; PHOTOEXCITATION; PHOTOVOLTAIC CELLS; PHOTOVOLTAIC EFFECTS; PLATINUM; PLATINUM COMPOUNDS; POLYMERS; SOLAR CELLS; SWITCHING CIRCUITS;

SOLAR ENERGY;

EID: 67650077497     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.02.006     Document Type: Article

References (111)

1. Shaheen S.E., Ginley D.S., and Jabbour G.E. MRS Bull. 30 (2005) 10
2. Barnham K.W.J., Mazzer M., and Clive B. Nat. Mater. 5 (2006) 161
3. Robertson N. Angew. Chem., Int. Ed. 45 (2006) 2338
4. Grätzel M. Inorg. Chem. 44 (2005) 6841
5. Brabec C.J., Sariciftci N.S., and Hummelen J.C. Adv. Funct. Mater. 11 (2001) 15
6. Coakley K.M., and McGehee M.D. Chem. Mater. 16 (2004) 4533
7. Günes S., Neugebauer H., and Sariciftci N.S. Chem. Rev. 107 (2007) 1324
8. Winder C., and Saricftci N.S. J. Mater. Chem. 14 (2004) 1077
9. Thompson B.C., and Frechet J.M.J. Angew. Chem., Int. Ed. 47 (2008) 58 and references therein
10. Kim J.Y., Kim S.H., Lee H.H., Lee K., Ma W., Gong X., and Heeger A.J. Adv. Mater. 18 (2006) 572
11. Reyes-Reyes M., Kim K., and Carroll D.J. Appl. Phys. Lett. 87 (2005) 083506
12. Kim Y., Cook S., Tuladhar S.M., Choulis S.A., Nelson J., Durrant J.R., Bradley D.D.C., Giles M., McCulloch I., Ha C.S., and Ree M. Nat. Mater. 5 (2006) 197
13. Li G., Shrotriya V., Huang J., Yao Y., Moriarty T., Emery K., and Yang Y. Nat. Mater. 4 (2005) 864
14. Li G., Shortriya V., Yao Y., and Yang Y.J. J. Appl. Phys. 98 (2005) 043704
15. Kim Y., Choulis S.A., Nelson J., Bradley D.D.C., Cook S., and Durrant J.R. Appl. Phys. Lett. 86 (2005) 063502
16. de Bettignies R., Leroy J., Firon M., and Sentein C. Synthetic Met. 156 (2006) 510
17. Mihailetchi V.D., Xie H., de Boer B., Popescu L.M., Hummelen J.C., Blom P.W.M., and Koster L.J.A. Appl. Phys. Lett. 89 (2006) 012107
18. von Hauff E., Parisi J., and Dyakonov V.J. J. Appl. Phys. 100 (2006) 043702
19. Kim K., Liu J., Namboothiry M.A.G., and Carroll D.L. Appl. Phys. Lett. 90 (2007) 163511
20. Harvey P.D., and Fortin D. Coord. Chem. Rev. 171 (1998) 351
21. Chan W.-K., Hui C.S., Man K.Y.K., Cheng K.W., Wong H.L., Zhu N., and Djurišić A.B. Coord. Chem. Rev. 249 (2005) 1351
22. Tse C.W., Man K.Y.K., Cheng K.W., Mak C.S.K., Chan W.K., Yip C.T., Liu Z.T., and Djurišić A.B. Chem. Eur. J. 13 (2007) 328
23. Guo F., Kim Y.G., Reynolds J.R., and Schanze K.S. Chem. Commun. (2006) 1887
24. Köhler A., Wittmann H.F., Friend R.H., Khan M.S., and Lewis J. Synthetic Met. 77 (1996) 147
25. Köhler A., Wittmann H.F., Friend R.H., Khan M.S., and Lewis J. Synthetic Met. 67 (1994) 245
26. Chawdhury N., Köhler A., Friend R.H., Wong W.-Y., Lewis J., Younus M., Raithby P.R., Corcoran T.C., Al-Mandhary M.R.A., and Khan M.S. J. Chem. Phys. 110 (1999) 4963
27. Chawdhury N., Younus M., Raithby P.R., Lewis J., and Friend R.H. Opt. Mater. 9 (1998) 498
28. Younus M., Köhler A., Cron S., Chawdhury N., Al-Mandhary M.R.A., Khan M.S., Lewis J., Long N.J., Friend R.H., and Raithby P.R. Angew. Chem., Int. Ed. 37 (1998) 3036
29. Köhler A., Younus M., Al-Mandhary M.R.A., Raithby P.R., Khan M.S., and Friend R.H. Synthetic Met. 101 (1999) 246
30. Wong W.-Y. Dalton Trans. (2007) 4495
31. Wong W.-Y., Wang X.-Z., He Z., Djurišić A.B., Yip C.-T., Cheung K.-Y., Wang H., Mak C.S.-K., and Chan W.-K. Nat. Mater. 6 (2007) 521
32. Wong W.-Y., Wang X.-Z., He Z., Chan K.-K., Djurišić A.B., Cheung K.-Y., Yip C.-T., Ng A.M.-C., Xi Y.Y., Mak C.S.K., and Chan W.-K. J. Am. Chem. Soc. 129 (2007) 14372
33. Wong W.-Y. Macromol. Chem. Phys. 209 (2008) 14
34. Wong W.-Y., Wang X.-Z., Zhang H.-L., Cheung K.-Y., Fung M.-K., Djurišić A.B., and Chan W.-K. J. Organomet. Chem. 693 (2008) 3603
35. Li L., Ho C.-L., Wong W.-Y., Cheung K.-Y., Fung M.-K., Lam W.-T., Djurisic A.B., and Chan W.-K. Adv. Funct. Mater. 18 (2008) 2824
36. Wang X.-Z., Wong W.-Y., Cheung K.-Y., Fung M.-K., Djurisic A.B., and Chan W.-K. Dalton Trans. (2008) 5484
37. Guo F., Ogawa K., Kim Y.-G., Danilov E.O., Castellano F.N., Reynolds J.R., and Schanze K.S. Phys. Chem. Chem. Phys. 9 (2007) 2724
38. Manners I. Science 294 (2001) 1664
39. Nguyen P., Gómez-Elipe P., and Manners I. Chem. Rev. 99 (1990) 1515
40. Kingsborough R.P., and Swager T.M. Prog. Inorg. Chem. 48 (1999) 123
41. Abd-El-Aziz A.S. Macromol. Rapid Commun. 23 (2002) 995
42. Holliday B.J., and Swager T.M. Chem. Commun. (2005) 23
43. Fustin C.-A., Guillet P., Schubert U.S., and Gohy J.-F. Adv. Mater. 19 (2007) 1665
44. Abd-El-Aziz A.S., and Todd E.K. Coord. Chem. Rev. 246 (2003) 3
45. Abd-El-Aziz A.S., Carraher C.E., Pittman Jr. C.U., and Zeldin Jr. M. Macromolecules Containing Metal and Metal-Like Elements vol. 5 (2005), Wiley-Interscience, New Jersey
46. Wolf M.O. J. Inorg. Organomet. Polym. Mater. 16 (2006) 189
47. In: Abd-El-Aziz A.S., and Manners I. (Eds). Frontiers in Transition Metal-Containing Polymers (2007), Wiley-Interscience, New Jersey
48. Zhou Q., Hou Q., Zheng L., Deng X., Yu G., and Cao Y. Appl. Phys. Lett. 84 (2004) 1653
49. Svensson M., Zhang F., Veenstra S.C., Verhees W.J.H., Hummelen J.C., Kroon J.M., Inganäs O., and Anderson M.R. Adv. Mater. 15 (2003) 988
50. Zhang F., Mammo W., Andersson L.M., Admassie S., Andersson M.R., and Inganäs O. Adv. Mater. 18 (2006) 2169
51. Mühlbacher D., Scharber M., Morana M., Zhu Z., Waller D., Gaudiana R., and Brabec C. Adv. Mater. 18 (2006) 2884
52. Campoy-Quiles M., Ferenczi T., Agostinelli T., Etchegoin P.G., Kim Y., Anthopoulos T.D., Stavrinou P.N., Bradley D.D.C., and Nelson J. Nat. Mater. 7 (2008) 158
53. Chang Y.-T., Hsu S.-L., Su M.-H., and Wei K.-H. Adv. Funct. Mater. 17 (2007) 3326
54. Kim J.Y., Lee K., Coates N.E., Moses D., Nguyen T.-Q., Dante M., and Heeger A.J. Science 317 (2007) 222
55. Nanjo M., Cyr P.W., Liu K., Sargent E.H., and Manners I. Adv. Funct. Mater. 18 (2008) 470
56. Sainsbury M. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry vol. 3 (1984), Pergamon, Oxford, UK 995
57. Albery W.J., Foulds A.W., Hall K.J., Hillman A.R., Edgell R.G., and Orchard A.F. Nature 282 (1979) 793
58. Ionescu M., and Mantsch H. Adv. Heterocycl. Chem. 8 (1967) 83
59. Bodea C., and Silberg I. Adv. Heterocycl. Chem. 9 (1968) 321
60. Valzelli L., and Garattini S. In: Clark W.G. (Ed). Principles of Psychopharmacology (1970), Academic Press, New York 255
61. Okafor C.O. Heterocycles 7 (1977) 391
62. Eckstein Z., and Urbanski T. Adv. Heterocycl. Chem. 23 (1978) 1
63. Szabo J. Chem. Heterocycl. Comp. USSR (Engl. Trans.) 15 (1979) 291
64. Sainsbury M. In: Sainsbury M. (Ed). Rodd's Chemistry of Carbon Compounds. 2nd ed. vol. 4 (1998), Elsevier, Amsterdam 575
65. McIntyre R., and Gerischer H. Ber. Bunsen Ges. Phys. Chem. 88 (1984) 963
66. Sailer M., Nonnenmacher M., Oeser T., and Müller T.J.J. Eur. J. Org. Chem. (2006) 423
67. Sailer M., Franz A.W., and Müller T.J.J. Chem. Eur. J. 14 (2008) 2602
68. Daub J., Engl R., Kurzawa J., Miller S.E., Schneider S., Stockmann A., and Wasielewski M.R.J. Phys. Chem. A 105 (2001) 5655
69. Chen P., Westmoreland D., Danielson E., Schanze K.S., Anthon D., Neveux P.E.J., and Meyer T.J. Inorg. Chem. 26 (1987) 1116
70. Krämer C.S., and Müller T.J.J. Eur. J. Org. Chem. (2003) 3534
71. McGarrah J.E., Kim Y.J., Hissler M., and Eisenberg R. Inorg. Chem. 40 (2001) 4510
72. McGarrah J.E., and Eisenberg R. Inorg. Chem. 42 (2003) 4355
73. Wadas T.J., Chakraborty S., Lachicotte R.J., Wang Q.M., and Eisenberg R. Inorg. Chem. 44 (2005) 2628
74. Bates W.D., Chen P., Dattelbaum D.M., Jones Jr. W.E., and Meyer T.J. J. Phys. Chem. A 103 (1999) 5227
75. Pfennig B.W., Chen P.Y., and Meyer T.J. Inorg. Chem. 35 (1996) 2898
76. Jones Jr. W.E., Chen P., and Meyer T.J. J. Am. Chem. Soc. 114 (1992) 387
77. Brun A.M., Harriman A., Heitz V., and Sauvage J.P. J. Am. Chem. Soc. 113 (1991) 8657
78. Knorr A., and Daub J. Angew. Chem., Int. Ed. Engl. 107 (1995) 2925
79. Knorr A., and Daub J. Angew. Chem., Int. Ed. Engl. 34 (1995) 2664
80. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
81. Long N.J., and Williams C.K. Angew. Chem., Int. Ed. 42 (2003) 2586
82. Manners I. Synthetic Metal-Containing Polymers (2004), Wiley-VCH, Weinheim
83. Wong W.-Y., and Ho C.-L. Coord. Chem. Rev. 250 (2006) 2627
84. Wong W.-Y. J. Inorg. Organomet. Polym. Mater. 15 (2005) 197
85. Davies S.J., Johnson B.F.G., Khan M.S., and Lewis J. J. Chem. Soc., Chem. Commun. (1991) 187
86. Lewis J., Khan M.S., Johnson B.F.G., Marder T.B., Fyfe H.B., Wittmann F., Friend R.H., and Dray A.E. J. Organomet. Chem. 425 (1992) 165
87. Fujikura Y., Sonogashira K., and Hagihara N. Chem. Lett. (1975) 1067
88. Sonogashira K., Takahashi S., and Hagihara N. Macromolecules 10 (1977) 879
89. Sonogashira K., Kataoka S., Takahashi S., and Hagihara N.J. J. Organomet. Chem. 160 (1978) 319
90. Khan M.S., Al-Mandhary M.R.A., Al-Suti M.K., Ahrens B., Mahon M.F., Male L., Raithby P.R., Boothby C.E., and Köhler A. Dalton Trans. (2003) 74
91. Zade S.S., and Bendikov M. Org. Lett. 8 (2006) 5243
92. Bäuerle P. Adv. Mater. 4 (1992) 102
93. Lahti P.M., Obrzut J., and Karasz F.E. Macromolecules 20 (1987) 2023
94. Wilson J.S., Chawdhury N., Al-Mandhary M.R.A., Younus M., Khan M.S., Raithby P.R., Köhler A., and Friend R.H. J. Am. Chem. Soc. 123 (2001) 9412
95. Khan M.S., Al-Mandhary M.R.A., Al-Suti M.K., Al-Battashi F.R., Al-Saadi S., Ahrens B., Bjernemose J.K., Mahon M.F., Raithby P.R., Younus M., Chawdhury N., Köhler A., Marseglia E.A., Tedesco E., Feeder N., and Teat S.J. Dalton Trans. (2004) 2377
96. Hou J., Tan Z., Yan Y., He Y., Yang C., and Li Y. J. Am. Chem. Soc. 128 (2006) 4911
97. Van de Walle C.G., and Neugebauer J. Nature (London) 423 (2003) 626
98. Garcia P., Pernaut J.M., Hapiot P., Wintgens V., Valat P., Garnier F., and Delabouglise D. J. Phys. Chem. 97 (1993) 513
99. Jestin I., Frère P., Mercier N., Levillain E., Stievenard D., and Roncali J. J. Am. Chem. Soc. 120 (1998) 8150
100. Diaz A.F., Crowley J., Bargon J., Gardini G.P., and Torrance J.B. J. Electroanal. Chem. 121 (1981) 355
101. Harima Y., Kim D.-H., Tsutitori Y., Jiang X., Patil R., Ooyama Y., Ohshita J., and Kunai A. Chem. Phys. Lett. 420 (2006) 387
102. Perepichka I.F., Perepichka D.F., Meng H., and Wudl F. Adv. Mater. 17 (2005) 2281
103. McCullough R.D. Adv. Mater. 10 (1998) 9316
104. Stott T.-L., and Wolf M.O. Coord. Chem. Rev. 246 (2003) 89
105. Wong W.-Y., Lu G.-L., Ng K.-F., Choi K.-H., and Lin Z. J. Chem. Soc., Dalton Trans. (2001) 3250
106. Koster L.J.A., Mihailetchi V.D., Ramaker R., and Blom P.W.M. Appl. Phys. Lett. 86 (2005) 123509-123511
107. Dyakonov V. Appl. Phys. A 79 (2004) 21
108. Xue J., Uchida S., Rand B.P., and Forrest S.R. Appl. Phys. Lett. 84 (2004) 3013
109. Dawson W.R., and Windsor M.W. J. Phys. Chem. 72 (1968) 3251
110. Chatt J., and Hayter R.G. J. Chem. Soc., Dalton Trans. (1961) 896
111. Chatt J., and Shaw B.L. J. Chem. Soc. (1960) 4020