Photoinduced Electron/Energy Transfer within Light-Harvesting Dendrimers

doi:10.7517/j.issn.1674-0475.2011.04.246

Abstract

Abstract: Dendrimers are well-defined tree-like macromolecules having numerous chain ends all emanating from a single core,which makes them an attractive candidate for light-harvesting applications.More importantly,their synthesis is controllable and the accurate positioning of chromophores can be achieved.Photoinduced electron transfer and energy transfer are main processes involved in photosynthesis.Studies on these processes in dendritic systems are important for the future application of dendrimers in optoelectronic devices.In this Focus Review we will discuss recent advances of light-harvesting dendrimers and emphasize the energy transfer and electron transfer characteristics in these systems.

Key words: dendrimer, light-harvesting, energy transfer, electron transfer

CLC Number:

LI Yi, ZHANG Xiao-hui, ZENG Yi, CHEN Jin-ping, LI Ying-ying. Photoinduced Electron/Energy Transfer within Light-Harvesting Dendrimers[J]. Imaging Science and Photochemistry, 2011, 29(4): 246-269.

References

[1] Mcdermott G,Prince S M,Freer A A,et al.Crystal-structure of an integral membrane light-harvesting complexfrom photosynthetic bacteria[J].Nature,1995,374(6522):517-521.
[2] Hu X C,Damjanovic A,Ritz T,et al.Architecture and mechanism of the light-harvesting apparatus of purplebacteria[J].Proc.Natl.Acad.Sci.USA,1998,95(11):5935-5941.
[3] Kaanumalle L S,Nithyanandhan J,Pattabiraman M,et al.Water-soluble dendrimers as photochemical reactionmedia:chemical behavior of singlet and triplet radical pairs inside dendritic reaction cavities[J].J.Am.Chem.Soc.,2004,126(29):8999-9006.
[4] Tekade R K,Kumar P V,Jain N K.Dendrimers in oncology:An expanding horizon[J].Chem.Rev.,2009,109(1):49-87.
[5] Yuan Z,Zheng S J,Zeng Y,et al.Photosensitized oxidation of alkenes with dendrimers as microreactors:con-trollable selectivity between energy and electron transfer pathway[J].New J.Chem.,2010,34(4):718-722.
[6] 刘白宁,游长江,韩永滨,等.树枝形聚合物修饰双8-羟基喹啉衍生物的合成及稳态光物理性质研究[J].影像科学与光化学,2005,23(2):129-135.Liu B N,You C J,Han Y B,et al.Synthesis and studies on the photophysical properties of dendritic bis-(8-hydroxyquinoline)derivatives[J].Imaging Science and Photochemistry,2005,23(2):129-135.
[7] 袁钊,曾毅,陈金平,等.以尼罗红为探针对新型两亲性树枝形聚合物微环境的研究[J].影像科学与光化学,2010,28(5):343-353.Yuan Z,Zeng Y,Chen J P,et al.Investigation of the microenvironment of novel amphiphilic dendrimers with nilered as a probe[J].Imaging Science and Photochemistry,2010,28(5):343-353.
[8] 郑少君,曾毅,李明,等.尼罗红为探针对芳醚树枝形聚合物微环境的研究[J].影像科学与光化学,2009,27(1):1-7.Zheng S J,Zeng Y,Li M,et al.Study of microenvironment of dendrimers with nile red as the fluoresenece probe[J].Imaging Science and Photochemistry,2009,27(1):1-7.
[9] Tomalia D A,Naylor A M,Goddard W A.Starburst dendrimers-molecular-level control of size,shape,surface-chemistry,topology,and flexibility from atoms to macroscopic matter[J].Angew.Chem.Int.Ed.,1990,29(2):138-175.
[10] Newkome G R,Moorefield C N,V gtle F.Dendrimers and Dendrons:Concepts,Syntheses,Applications[M].Weinheim:Wiley-VCH,2001.
[11] Frechet J M.Functional polymers and dendrimers:reactivity,molecular architecture,and interfacial energy[J].Science,1994,263(5154):1710-1715.
[12] Katz J L,Choi S,Jortner J,et al.Triplet exciton bands in aromatic crystals[J].J.Chem.Phys.,1963,39(7):1897-1899.
[13] Dexter D L.A theory of sensitized luminescence in solids[J].J.Chem.Phys.,1953,21(5):836-850.
[14] Förster T.Fluorenzenz Organishe Verbindugugeh[M].Gottingen:Vandenhoech and Ruprech,1951.
[15] Fox M A,Chanon,M.Photoinduced Electron Transfer Part A.Conceptual Basis[M].Amsterdam:Elsevi-er,1988.
[16] Rehm D,Weller A.Kinetics of fluorescence quenching by electron and H-atom transfer[J].Isr.J.Chem.,1970,8(2):259-271.
[17] Balzani V,Campagna S,Denti G,et al.Designing dendrimers based on transition metal complexes.Light-har-vesting properties and predetermined redox patterns[J].Acc.Chem.Res.,1998,31(1):26-34.
[18] Denti G,Campagna S,Serroni S,et al.Decanuclear homometallic and heterometallic polypyridine complexes-syntheses,absorption-spectra,luminescence,electrochemical oxidation,and intercomponent energy-transfer[J].J.Am.Chem.Soc.,1992,114(8):2944-2950.
[19] Balzani V,Bergamini G,Ceroni P,et al.Electronic spectroscopy of metal complexes with dendritic ligands[J].Coord.Chem.Rev.,2007,251(3-4):525-535.
[20] Campagna S,Di Pietro C,Loiseau F,et al.Recent advances in luminescent polymetallic dendrimers containingthe 2,3-bis(2'-pyridyl)pyrazine bridging ligand[J].Coord.Chem.Rev.,2002,229(1-2):67-74.
[21] McClenaghan N D,Loiseau F,Puntoriero F,et al.Light-harvesting metal dendrimers appended with additionalorganic chromophores:a tetranuclear heterometallic first-generation dendrimer exhibiting unusual absorptionfeatures[J].Chem.Commun.,2001,(24):2634-2635.
[22] Serroni S,Campagna S,Puntoriero F,et al.Dendrimers based on ruthenium(II)and osmium(II)polypyridinecomplexes and the approach of using complexes as ligands and complexes as metals[J].Chem.Soc.Rev.,2001,30(6):367-375.
[23] Xu Z F,Moore J S.Stiff dendritic macromolecules.4.design and synthesis of a convergent and directional mo-lecular antenna[J].Acta Polym.,1994,45(2):83-87.
[24] Xu Z F,Moore J S.Stiff dendritic macromolecules.3.rapid construction of large-size phenylacetylene dendrim-ers up to 12.5 nanometers in molecular diameter[J].Angew.Chem.Int.Ed.,1993,32(9):1354-1357.
[25] Devadoss C,Bharathi P,Moore J S.Energy transfer in dendritic macromolecules:molecular size effects and therole of an energy gradient[J].J.Am.Chem.Soc.,1996,118(40):9635-9644.
[26] Peng Z H,Pan Y C,Xu B B,et al.Synthesis and optical properties of novel unsymmetrical conjugated dendrim-ers[J].J.Am.Chem.Soc.,2000,122(28):6619-6623.
[27] Melinger J S,Pan Y C,Kleiman V D,et al.Optical and photophysical properties of light-harvesting phenylacet-ylene monodendrons based on unsymmetrical branching[J].J.Am.Chem.Soc.,2002,124(40):12002-12012.
[28] Wang J L,Yan J,Tang Z M,et al.Gradient shape-persistent pi-conjugated dendrimers for light-harvesting:synthesis,photophysical properties,and energy funneling[J].J.Am.Chem.Soc.,2008,130(30):9952-9962.
[29] Kawa M,Fréchet J M J.Self-assembled lanthanide-cored dendrimer complexes:enhancement of the lumines-cence properties of lanthanide ions through site-isolation and antenna effects[J].Chem.Mater.,1998,10(1):286-296.
[30] Jiang D L,Aida T.Morphology-dependent photochemical events in aryl ether dendrimer porphyrins:coopera-tion of dendron subunits for singlet energy transduction[J].J.Am.Chem.Soc.,1998,120(42):10895-10901.
[31] Adronov A,Gilat S L,Fréchet J M J,et al.Light harvesting and energy transfer in laser-dye-labeled poly(arylether)dendrimers[J].J.Am.Chem.Soc.,2000,122(6):1175-1185.
[32] Dichtel W R,Hecht S,Fréchet J M J.Functionally layered dendrimers:a new building block and its applicationto the synthesis of multichromophoric light-harvesting systems[J].Org.Lett.,2005,7(20):4451-4454.
[33] Larsen J,Bruggemann B,Khoury T,et al.Structural induced control of energy transfer within Zn(II)-porphy-rin dendrimers[J].J.Phys.Chem.A,2007,111(42):10589-10597.
[34] Oar M A,Serin J A,Dichtel W R,et al.Photosensitization of singlet oxygen via two-photon-excited fluores-cence resonance energy transfer in a water-soluble dendrimer[J].Chem.Mater.,2005,17(9):2267-2275.
[35] Yeow E K L,Ghiggino K P,Reek J N H,et al.The dynamics of electronic energy transfer in novel multipor-phyrin functionalized dendrimers:a time-resolved fluorescence anisotropy[J].J.Phys.Chem.B,2000,104(12):2596-2606.
[36] Yuan M J,Yin X D,Zheng H Y,et al.Light harvesting and efficient energy transfer in dendritic systems:newstrategy for functionalized near-infrared BF2-azadipyrromethenes[J].Chem.Asian J.,2009,4(5):707-713.
[37] Liu D J,De Feyter S,Cotlet M,et al.Fluorescence and intramolecular energy transfer in polyphenylene den-drimers[J].Macromolecules,2003,36(16):5918-5925.
[38] Cotlet M,Gronheid R,Habuchi S,et al.Intramolecular directional forster resonance energy transfer at the sin-gle-molecule level in a dendritic system[J].J.Am.Chem.Soc.,2003,125(44):13609-13617.
[39] Gronheid R,Hofkens J,Kohn F,et al.Intramolecular Forster energy transfer in a dendritic system at the singlemolecule level[J].J.Am.Chem.Soc.,2002,124(11):2418-2419.
[40] De Schryver F C,Vosch T,Cotlet M,et al.Energy dissipation in multichromophoric single dendrimers[J].Acc.Chem.Res.,2005,38(7):514-522.
[41] Maus M,De R,Lor M,et al.Intramolecular energy hopping and energy trapping in polyphenylene dendrimerswith multiple peryleneimide donor chromophores and a terryleneimide acceptor trap chromophore[J].J.Am.Chem.Soc.,2001,123(31):7668-7676.
[42] Maus M,Mitra S,Lor M,et al.Intramolecular energy hopping in polyphenylene dendrimers with an increasingnumber of peryleneimide chromophores[J].J.Phys.Chem.A,2001,105(16):3961-3966.
[43] Surin N M,Borshchev O V,Luponosov Y N,et al.Luminescence spectral properties of dendritic oligothiophen-esilane macromolecules[J].Russ.J.Phys.Chem.A,2010,84(11):1979-1985.
[44] Borshchev O V,Ponomarenko S A,Kleymyuk E A,et al.Branched oligothiophene silanes with the efficientnonradiative energy transfer between the fragments[J].Russ.Chem.Bull.,2010,59(4):797-805.
[45] Luponosov Y N,Ponomarenko S A,Surin N M,et al.First organosilicon molecular antennas[J].Chem.Ma-ter.,2009,21(3):447-455.
[46] Bergamini G,Ceroni P,Maestri M,et al.Forward(singlet-singlet)and backward(triplet-triplet)energy trans-fer in a dendrimer with peripheral naphthalene units and a benzophenone core[J].Photochem.Photobiol.Sci.,2004,3(9):898-905.
[47] Giansante C,Ceroni P,Balzani V,et al.Photophysical,photochemical,and electrochemical properties of den-drimers with a dimethoxybenzil core[J].New J.Chem.,2007,31(7):1250-1258.
[48] Chen J P,Li S Y,Zhang L,et al.Light-harvesting and photoisomerization in benzophenone and norbornadiene-labeled poly(aryl ether)dendrimers via intramolecular triplet energy transfer[J].J.Am.Chem.Soc.,2005,127(7):2165-2171.
[49] Zhang L,Chen J P,Li S Y,et al.Photophysical and photochemical studies on bis(dendron)poly(aryl ether)dendrimers:Intramolecular triplet energy transfer in poly(aryl ether)dendrimers via a folded conformation[J].J.Photochem.Photobiol.,A,2006,181(2-3):429-436.
[50] Chen J,Li S,Zhang L,Li Y Y,et al.Direct observation of the intramolecular triplet-triplet energy transfer inpoly(aryl ether)dendrimers[J].J.Phys.Chem.B,2006,110(9):4047-4053.
[51] Kwon T H,Kim M K,Kwon J,et al.Highly efficient light-harvesting system based on a phosphorescent accep-tor coupled with dendrimer donors via singlet-singlet and triplet-triplet energy transfer[J].Chem.Mater.,2007,19(15):3673-3680.
[52] Stewart G M,Fox M A.Chromophore-labeled dendrons as light harvesting antennae[J].J.Am.Chem.Soc.,1996,118(18):4354-4360.
[53] Vicinelli V,Maestri M,Balzani V,et al.Dendrimers with a 4,4-′bipyridinium core and electron-donor bran-ches.Electrochemical and spectroscopic properties[J].New J.Chem.,2001,25(8):989-993.
[54] Ghaddar T H,Wishart J F,Thompson D W,et al.A dendrimer-based electron antenna:paired electron-transferreactions in dendrimers with a 4,4'-bipyridine core and naphthalene peripheral groups[J].J.Am.Chem.Soc.,2002,124(28):8285-8289.
[55] Guldi D M,Swartz A,Luo C,et al.Rigid dendritic donor-acceptor ensembles:control over energy and electrontransduction[J].J.Am.Chem.Soc.,2002,124(36):10875-10886.
[56] Armaroli N,Accorsi G,Clifford J N,et al.Structure-dependent photoinduced electron transfer in fulleroden-drimers with light-harvesting oligophenylenevinylene terminals[J].Chem.Asian J.,2006,1(4):564-574.
[57] Qu J Q,Pschirer N G,Liu D J,et al.Dendronized perylenetetracarboxdiimides with peripheral triphenylaminesfor intramolecular energy and electron transfer[J].Chem.Eur.J.,2004,10(2):528-537.
[58] Thomas K R J,Thompson A L,Sivakumar A V,et al.Energy and electron transfer in bifunctional non-conjuga-ted dendrimers[J].J.Am.Chem.Soc.,2005,127(1):373-383.
[59] Chen J,Chen J,Li S,et al.Conversion of intramolecular singlet electron transfer at room temperature into trip-let energy transfer at 77 K:photoisomerization in norbornadiene-and carbazole-labeled poly(aryl ether)den-drimers[J].J.Phys.Chem.B,2006,110(10):4663-4670.
[60] Chen J P,Zhang L,Li S Y,et al.Valence isomerization in dendrimers by photo-induced electron transfer andenergy transfer from the dendrimer backbone to the core[J].J.Photochem.Photobiol.,A,2007,185(1):67-75.
[61] Li Y Y,Han L,Chen J P,et al.Study on the extent of folding back conformation in poly(aryl ether)dendrimersby intramolecular electron transfer and exciplex formation[J].Macromolecules,2007,40(26):9384-9390.
[62] Li M,Li Y Y,Zeng Y,et al.Intramolecular exciplex formation induced by the folding-back conformation of poly(aryl ether)dendrimers[J].J.Phys.Chem.C,2009,113(27):11554-11559.
[63] Bagui M,Dutta T,Chakraborty S,et al.Synthesis and optical properties of triphenylene-based dendritic donorperylene diimide acceptor systems[J].J.Phys.Chem.A,2011,115(9):1579-1592.
[64] Schenning A P H J,Peeters E,Meijer E W.Energy transfer in supramolecular assemblies of oligo(p-phenylenevinylene)s terminated poly(propylene imine)dendrimers[J].J.Am.Chem.Soc.,2000,122(18):4489-4495.
[65] Hahn U,Gorka M,Vogtle F,et al.Light-harvesting dendrimers:efficient intra-and intermolecular energy-transfer processes in a species containing 65 chromophoric groups of four different types[J].Angew.Chem.Int.Ed.,2002,41(19):3595-3598.
[66] Giansante C,Ceroni P,Balzani V,et al.Self-assembly of a light-harvesting antenna formed by a dendrimer,aRu-II complex,and a Nd-III ion[J].Angew.Chem.Int.Ed.,2008,47(29):5422-5425.
[67] Branchi B,Ceroni P,Balzani V,et al.A light-harvesting antenna resulting from the self-assembly of five lumi-nescent components:a dendrimer,two clips,and two lanthanide ions[J].Chem.Eur.J.,2010,16(20):6048-6055.
[68] Zeng Y,Li Y Y,Li M,et al.Enhancement of energy utilization in light-harvesting dendrimers by the pseudoro-taxane formation at periphery[J].J.Am.Chem.Soc.,2009,131(25):9100-9106.