Abstract
The fluorescence properties of double layer-type dendrimers with carbazole as the outer layer and phenylazomethine as the inner layer of the dendron with a zinc porphyrin core were studied. Based on the fluorescence quantum yield (solution), the effect of the bulky dendron to inhibit the interaction of the chromophores was confirmed. Additionally, the efficient light-harvesting property of the double layer-type dendron was revealed by the fluorescence measurement at several excitation wavelengths. These dendrimers were used as an emitting-layer in an OLED device. The electroluminescence of the core porphyrin was observed and it was shown that the double layer-type dendrimer with a luminescent core has the potential to be a hole-transporting/emitting material.
Similar content being viewed by others
References
C.W. Tang, S.A. Van Slyke, Appl. Phys. Lett. 51, 913 (1987)
A.P. Kulkarni, C.J. Tonzola, A. Babel, S.A. Jenekhe, Chem. Mater. 16, 4556 (2004)
Y. Shirota, H. Kageyama, Chem. Rev. 107, 953 (2007)
J. Kido, K. Hongawa, K. Okuyama, K. Nagai, Appl. Phys. Lett. 63, 2627 (1993)
J. Kido, M. Kimura, K. Nagai, Science 267, 1332 (1995)
B. Geffroy, P. le Roy, C. Prat, Polym. Int. 55, 572 (2006)
O. Nuyken, S. Jungermann, V. Wiederhirn, E. Bacher, K. Meerholz, Monatsh. Chem. 137, 811 (2006)
K.Y. Hwang, M.H. Lee, H. Jang, Y. Sung, J.S. Lee, S.H. Kim, Y. Do, Dalton Trans. 14, 1818 (2008)
M. Ichikawa, S. Fujimoto, Y. Miyazaki, T. Koyama, N. Yokoyama, T. Miki, Y. Taniguchi, Org. Electron. 9, 77 (2008)
V.I. Adamovich, S.R. Cordero, P.I. Djurovich, A. Tamayo, M.E. Thompson, B.W. D’Andrade, S.R. Forrest, Org. Electron. 4, 77 (2003)
Y. Hamada, T. Sano, M. Fujita, T. Fujii, Y. Nishio, K. Shibata, Chem. Lett. 22, 905 (1993)
J. Kido, Y. Iizumi, Chem. Lett. 26, 963 (1997)
N. Nakmura, S. Wakabayashi, K. Miyairi, T. Fujii, Chem. Lett. 23, 1741 (1994)
C. Hosokawa, H. Higashi, H. Nakamura, T. Kusumoto, Appl. Phys. Lett. 67, 3853 (1995)
K.R.J. Thomas, J.T. Lin, Y.T. Tao, C.W. Ko, Adv. Mater. 12, 1949 (2000)
J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. MacKay, R.H. Friend, P.L. Burn, A.B. Holmes, Nature 347, 539 (1990)
N.C. Greenham, S.C. Moratti, D.D.C. Bradley, R.H. Friend, A.B. Holmes, Nature 365, 628 (1993)
N. Tessler, G.J. Denton, R.H. Friend, Nature 382, 695 (1996)
S. Welter, K. Brunner, J.W. Hofstraat, L. De Cola, Nature 421, 54 (2003)
D.A. Tomalia, Prog. Polym. Sci. 30, 294 (2005)
A.W. Bosman, H.M. Janssen, E.W. Meijer, Chem. Rev. 99, 1665 (1999)
M. Fischer, F. Vögtle, Angew. Chem., Int. Ed. 38, 884 (1999)
D.A. Tomalia, A.M. Naylor, W.A. Goddard III, Angew. Chem., Int. Ed. Engl 29, 138 (1990)
S.C. Lo, P.L. Burn, Chem. Rev. 107, 1097 (2007)
M. Thelakkat, Macromol. Mater. Eng. 287, 442 (2002)
J. Bettenhausen, P. Strohriegl, Adv. Mater. 8, 507 (1996)
N. Tamoto, C. Adachi, K. Nagai, Chem. Mater. 9, 1077 (1997)
J. Bettenhausen, P. Strohriegl, W. Brutting, H. Tokuhisa, T. Tsutsui, J. Appl. Phys. 82, 4957 (1997)
J. Bettenhausen, M. Greczmiel, M. Jandke, P. Strohriegl, Synth. Met. 91, 223 (1997)
M. Thelakkat, H.W. Schmidt, Adv. Mater. 10, 219 (1998)
M. Halim, J.N.G. Pillow, I.D.W. Samuel, P.L. Burn, Adv. Mater. 11, 371 (1999)
Y. Sakamoto, T. Suzuki, A. Miura, H. Fujikawa, S. Tokito, Y. Taga, J. Am. Chem. Soc. 122, 1832 (2000)
J.M. Lupton, L.R. Hemingway, I.D.W. Samuel, P.L. Burn, J. Mater. Chem. 10, 867 (2000)
H.C. Yeh, R.H. Lee, L.H. Chan, T.Y.J. Lin, C.T. Chen, E. Balasubramaniam, Y.T. Tao, Chem. Mater. 13, 2788 (2001)
J.M. Lupton, I.D.W. Samuel, R. Beavington, P.L. Burn, H. Bässler, Adv. Mater. 13, 258 (2001)
D. Ma, J.M. Lupton, I.D.W. Samuel, S.C. Lo, P.L. Burn, Appl. Phys. Lett. 81, 2285 (2002)
T.W. Kwon, M.M. Alam, S.A. Jenekhe, Chem. Mater. 16, 4657 (2004)
X.Y. Cao, X.H. Liu, X.H. Zhou, Y. Zhang, Y. Jiang, Y. Cao, Y.X. Cui, J. Pei, J. Org. Chem. 69, 6050 (2004)
D. Ma, Y. Hu, Y. Zhang, L. Wang, X. Jing, F. Wang, J.M. Lupton, I.D.W. Samuel, S. Lo, P.L. Burn, Synth. Met. 137, 1125 (2003)
A. Nantalaksakul, D.R. Reddy, C.J. Bardeen, S. Thayumanavan, Photosynth. Res. 87, 133 (2006)
A.W. Freeman, S.C. Koene, P.R.L. Malenfant, M.E. Thompson, J.M.J. Fréchet, J. Am. Chem. Soc. 122, 12385 (2000)
S. Setayesh, A.C. Grimsdale, T. Weil, V. Enkelmann, K. Müllen, F. Meghdadi, E.J.W. List, G. Leising, J. Am. Chem. Soc. 123, 946 (2001)
C.C. Kwok, M.S. Wong, Macromolecules 34, 6821 (2001)
A. Pogantsch, F.P. Wenzl, E.J.W. List, G. Leising, A.C. Grimsdale, K. Müllen, Adv. Mater. 14, 1061 (2002)
P. Du, W.H. Zhu, Y.Q. Xie, F. Zhao, C.F. Ku, Y. Cao, C.P. Chang, H. Tian, Macromolecules 37, 4378 (2004)
J.P.J. Markham, S.C. Lo, S.W. Magennis, P.L. Burn, I.D.W. Samuel, Appl. Phys. Lett. 80, 2645 (2002)
S.C. Lo, N.A.H. Male, J.P.J. Markham, S.W. Magennis, P.L. Burn, O.V. Salata, D.W. Samuel, Adv. Mater. 14, 975 (2002)
S.C. Lo, E.B. Namdas, P.L. Burn, I.D.W. Samuel, Macromolecules 36, 9721 (2003)
T.D. Anthopoulos, M.J. Frampton, E.B. Namdas, P.L. Burn, I.D.W. Samuel, Adv. Mater. 16, 557 (2004)
J.P.J. Markham, E.B. Namdas, T.D. Anthopoulos, I.D.W. Samuel, G.J. Richards, P.L. Burn, Appl. Phys. Lett. 85, 1463 (2004)
M.J. Frampton, E.B. Namdas, S.C. Lo, P.L. Burn, I.D.W. Samuel, J. Mater. Chem. 14, 2881 (2004)
N.D. McClenaghan, R. Passalacqua, F. Loiseau, S. Campagna, B. Verheyde, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 125, 5356 (2003)
F. Loiseau, S. Campagna, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 127, 11352 (2005)
T.H. Xu, R. Lu, X.P. Qiu, X.L. Liu, P.C. Xue, C.H. Tan, C.Y. Bao, Y.Y. Zhao, Eur. J. Org. Chem. 2006, 4014 (2006)
T. Konno, M.E. El-Khouly, Y. Nakamura, K. Kinoshita, Y. Araki, O. Ito, T. Yoshihara, S. Tobita, J. Nishimura, J. Phys. Chem. C 112, 1244 (2008)
J. Lu, P.F. Xia, P.K. Lo, Y. Tao, M.S. Wong, Chem. Mater. 18, 6194 (2006)
K.T. Wong, Y.H. Lin, H.H. Wu, F. Fungo, Org. Lett. 9, 4531 (2007)
K. Albrecht, K. Yamamoto, J. Photopoly. Sci. Technol. 19, 175 (2006)
K. Yamamoto, M. Higuchi, S. Shiki, M. Tsuruta, H. Chiba, Nature 415, 509 (2002)
M. Higuchi, S. Shiki, K. Ariga, K. Yamamoto, J. Am. Chem. Soc. 123, 4414 (2001)
K. Yamamoto, T. Imaoka, Bull. Chem. Soc. Jpn. 79, 511 (2006)
K. Albrecht, Y. Kasai, A. Kimoto, K. Yamamoto, Macromolecules 41, 3793 (2008)
A. Kimoto, J.S. Cho, M. Higuchi, K. Yamamoto, Macromolecules 37, 5531 (2004)
A. Kimoto, J.S. Cho, M. Higuchi, K. Yamamoto, Macromol. Symp. 209, 51 (2004)
A. Kimoto, J.S. Cho, K. Ito, D. Aoki, T. Miyake, K. Yamamoto, Macromol. Rapid Commun. 26, 597 (2005)
Q. Zhang, Y.F. Hu, Y.X. Cheng, G.P. Su, D.G. Ma, L.X. Wang, X.B. Jing, F.S. Wang, Synth. Met. 137, 1111 (2003)
J. Ding, J. Gao, Y. Cheng, Z. Xie, L. Wang, D. Ma, X. Jing, F. Wang, dv. Funct. Mater. 16, 575 (2006)
M.H. Tsai, Y.H. Hong, C.H. Chang, H.C. Su, C.C. Wu, A. Matoliukstyte, J. Simokaitiene, S. Grigalevicius, J.V. Grazulevicius, C.P. Hsu, Adv. Mater. 19, 862 (2007)
J.S. Cho, K. Takanashi, M. Higuchi, K. Yamamoto, Synth. Met. 150, 79 (2005)
N. Satoh, J.S. Cho, M. Higuchi, K. Yamamoto, J. Am. Chem. Soc. 125, 8104 (2003)
K. Albrecht, A. Kimoto, J.S. Cho, Y. Matsuura, K. Yamamoto, J. Photopolym. Sci. Technol. 21, 181 (2008)
A. Kimoto, K. Masachika, J.S. Cho, M. Higuchi, K. Yamamoto, Chem. Mater. 16, 5706 (2004)
T. Imaoka, R. Tanaka, S. Arimoto, M. Sakai, M. Fujii, K. Yamamoto, J. Am. Chem. Soc. 127, 13896 (2005)
S. Campagna, S. Serroni, F. Puntoriero, C. Di Pietro, V. Ricevuto, in Electron Transfer in Chemistry, vol. 5, ed. by V. Balzani (Wiley-VCH, Weinheim, 2001)
S.K. Lower, M.A. El-Sayed, Chem. Rev. 66, 199 (1966)
M.A. El-Sayed, J. Chem. Phys. 36, 573 (1962)
M.A. El-Sayed, J. Chem. Phys. 38, 2834 (1963)
S. Speiser, Chem. Rev. 96, 1953 (1996)
T.H. Förster, Discuss. Faraday Soc. 27, 7 (1959)
D.L. Dexter, J. Chem. Phys. 21, 836 (1953)
L. De Cola, P. Belser, in Electron Transfer in Chemistry, vol. 5, ed. by V. Balzani (Wiley-VCH, Weinheim, 2001)
3D model of ZnPG2-2 was optimized by a MOPAC (MM-AM1) calculation with the CAChe Worksystem ver. 5.04 (Fujitsu)
Acknowledgement
This work was partially supported by Grants-in-Aid for Scientific Research (Nos. 19205020, 19022034), the Core Research for Evolution Science and Technology (CREST) program of the Japan Science and Technology (JST) Agency, and Global COE program “High-Level Global Cooperation for Leading-Edge Platform on Access Space (C12)”.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Albrecht, K., Kasai, Y. & Yamamoto, K. The Fluorescence and Electroluminescence Properties of the Carbazole–Phenylazomethine Double Layer-Type Dendrimer. J Inorg Organomet Polym 19, 118–123 (2009). https://doi.org/10.1007/s10904-008-9239-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-008-9239-3