Synthesis and Studies on the Photophysical Properties of Dendritic bis-(8-Hydroxyquinoline) Derivatives

doi:10.7517/j.issn.1674-0475.2005.02.129

Abstract

Abstract: A series of poly (aryl ether) dendrimers with bis-(8-hydroxyquinoline) attached to the core, generation 1-3, were synthesized. The steady state photophysical properties of these compounds in various solvents were studied. The results indicated that the fluorescent quantum yield increased with the generation increases. The dendritic structure showed isolating effect on the core. The intramolecular energy transfer from the dendritic structure to the core was observed.

Key words: poly (aryl ether) dendrimers, bis-(8-hydroxyquinoline), energy transfer

CLC Number:

LIU Bai-ning, YOU Chang-jiang, HAN Yong-bin, CHEN Jin-ping, ZHANG Lu, YANG Guo-qiang, LI Yi. Synthesis and Studies on the Photophysical Properties of Dendritic bis-(8-Hydroxyquinoline) Derivatives[J]. Imaging Science and Photochemistry, 2005, 23(2): 129-135.

References

[1] Tomalia D A, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P. A new class of polymers: starburst-dendritic macromolecules[J].Polym.J., 1985,17: 117-132.
[2] Grayson S M, Fréchet J M J. Convergent dendrons and dendrimers: from synthesis to applications[J].Chem. Rev., 2001, 101: 3819-3867.
[3] Shortreed M R, Swallen S F, Shi Z Y, Tan W, Xu Z, Devadoss C, Moore J S, Kopelman R. Directed energy transfer funnels in dendrimeric antenna supermolecules[J].J.Phys.Chem. B, 1997,101: 6318-6322.
[4] Jiang D L, Aida T. Photoisomerization in dendrimers by harvesting of low-energy photons[J].Nature, 1997, 388: 454-456.
[5] Tomoyose Y, Jiang D L, Jin R H, Aida T, Yamashita T, Horie K, Yashima E, Okamoto Y. Aryl ether dendrimers with an interior metalloporphyrin functionality as a spectroscopic probe: interpenetrating interaction with dendritic imidazoles[J].Macromolecules, 1996,29: 5236-5238.
[6] Jin R H, Aida T, Inoue S. 'Caged' porphyrin: the first dendritic molecule having a core photochemical functionality[J].J. Chem. Soc., Chem. Commun., 1993, 1260-1262.
[7] Phillips J P. The reactions of 8-quinolinol[J].Chem. Rev., 1956, 56: 271-297.
[8] Kido J, Kimura M, Nagai K. Multilayer white light-emitting organic electroluminescent device[J].Science, 1995,267: 1332-1334.
[9] Tang C W, Vanslyke S A, Chen C H. Electroluminescence of doped organic thin films[J].J.Appl.Phys., 1989,65: 3610-3614.
[10] Hawker C J, Fréchet J M J. Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules[J].J. Am. Chem. Soc., 1990,112: 7638-7647.
[11] Phillips J P, Deye J F, Leach T. Chelating agents containing two 8-quinolinol functions[J].Analytica Chimica Acta, 1960,23: 131-135.
[12] Robert A W, Rose M E. A rapid, simple, and mild procedure for alkylation of phenols, alcohols, amides and acids[J].Tetrahedron, 1979, 35: 2169-2173.
[13] V^L-gtle F, Plevoets M, Nieger M, Azzellini G C, Credi A, De Cola L, De Marchis V, Venturi M, Balzani V. Dendrimers with a photoactive and redox-active [Ru (bpy)3] ²⁺-type core: photophysical properties, electrochemical behavior, and excited-state electron-transfer reactions[J].J.Am.Chem.Soc., 1999, 121: 6290-6298.
[14] Jiang D L, Aida T. Morphology-dependent photochemical events in aryl ether dendrimer porphyrins: cooperation of dendron subunits for singlet energy transduction[J].J. Am. Chem. Soc., 1998,120: 10895-10901.
[15] Devadoss C, Bharathi P, Moore J S. Energy transfer in dendritic macromolecules: molecular size effects and the role of an energy gradient[J].J.Am. Chem. Soc., 1996,118: 9635-9644.
[16] Stewart G M, Fox M A. Chromophore-labeled dendrons as light harvesting antennae[J].J. Am. Chem. Soc., 1996,118: 4354-4360.