Abstract
Tree-like dendrimers with decreasing number of chromophores from periphery to core is an attractive candidate for light-harvesting applications. Numerous dendritic designs with different kinds of light-collecting chromophores at periphery and an energy-sink at the core have been demonstrated with high energy transfer efficiency. These building blocks are now being developed for several applications such as light-emitting diodes, frequency converters and other photonic devices. This review outlines the efforts that are based on both conjugated and non-conjugated dendrimers.
Similar content being viewed by others
References
Adronov A and Fréchet MJ (2000) Light-harvesting dendrimers. Chem Commun 1701–1710
A Adronov, SL Gilat, JMJ Fréchet, L Ohta, FVR Neuwahl and GR Fleming, Light harvesting and energy transfer in laser-dye-labeled poly(aryl ether) dendrimers. J Am Chem Soc 122 (2000) 1175-1185
V Balzani, A Credi and M Venturi, Photoprocesses. Curr Opin Chem biol 1 (1997) 506-513
V Balzani, S Campagna, G Dendri, A Juris, S Serroni and M Venuri, Designing dendrimers based on transition metal complexes. Light-harvesting properties and predetermined redox patterns. Acc Chem Res 31 (1998) 26-34
V Balzani, P Ceroni, S Gestermann, M Gorka, C Kauffmann and F Vögtle, Fluorescent guests hosted in fluorescent dendrimers. Tetrahedron 58 (2002) 629-637
V Balzani, P Ceroni, M Maestri and V Vicinelli, Light-harvesting dendrimers. Curr Opin Chem biol 7 (2003a) 657-665
V Balzani, A Credi and M Venturi, Photoinduced charge separation and solar energy conversion. Molecular Devices and Machines: a Journey to Nanoworld. Weinheim, Germany: Wiley-VCH (2003b).
A Bar-Haim and J Klafter, Geometric versus energetic competition in light harvesting by dendrimers. J Phys Chem B 102 (1998a) 1662-1664
A Bar-Haim and J Klafter, Dendrimers as Light-harvesting Antannae. Journal of Luminescence 76 (1998b) 197-200
A Bar-Haim, J Klafter and R Kopaelman, Dendrimers as controlled artificial energy antennae. J Am Chem Soc 119 (1997) 6197-6198
J Barber and B Andersson, Revealing the blueprint of photosynthesis. Nature 370 (1994) 31-34
M Braun, S Atalick, DM Guldi, H Lanig, M Brettreich, S Burghardt, M Hatzimarinaki, E Ravanelli, M Prato, R Eldik van and A Hirsch, Electrostatic complexation and photoinduced electron transfer between Zn-cytochromo c and polyanionic fullerene dendrimers. Chem Eur J 9 (2003) 3867-3875
K Bronk and S Thayumanavan, Design and synthesis of nonconjugated monodendrons with triarylamine repeating units. Org Lett 3 (2001) 2057-2060
K Bronk and S Thayumanavan, Synthesis of nonconjugated dendrons with a redox gradient. J Org Chem 68 (2003) 5559-5567
M Choi, T Aida, T Yamazaki and I Yamazaki, A large dendritic multiporphyrin array as a mimic of the bacterial light-harvesting antenna complex: molecular design of an efficient energy funnel for visible photons. Angew Chem Int Ed 40 (2001) 3194-3198
M Cotlet, S Masuo, M Lor, E Fron, M Auweraer Van der, K Müllen, J Hofkens and FC Schryver De, Probing the influence of O2 on photoinduced reversible electron transfer in perylenediimide– triphenylamine-based dendrimers by single-molecule spectroscopy. Angew Chem Int Ed 43 (2004a) 6116-6120
M Cotlet, S Masuo, G Luo, J Hofkens, M Auweraer Van der, J Verhoeven, K Müllen, XS Xie and FC Schryver De, Probing Conformational dynamics in Single donor-acceptor Synthetic molecules by means of photoinduced reversible electron transfer. Proc Natl Acad Sci U.S.A 101 (2004b) 14343-14348
J Deisenhofer and H Michel, The photosynthetic reaction center from the purple bacterium rhodopseudomonas virus. Science 245 (1989) 1463-1473
J Deisenhofer, O Epp, K Miki, R Huber and H Michel, Structure of protein subunits in The photosynthetic reaction center of rhodopseudomonas-viridis at 3A resolution. Nature 318 (1985) 618-624
C Devadoss, P Bharathi and JS Moore, Energy transfer in dendritic macromolecules: molecular size effects and the role of an energy gradient. J Am Chem Soc 118 (1996) 9635-9644
MA Fox, Polymeric and supramolecular arrays for directional energy and electron-transport over macroscopic distances. Acc Chem Res 25 (1992) 569-574
AW Freeman, SC Koene, PRL Malenfant, ME Thompson and JMJ Fréchet, Dendrimer-containing light-emitting diodes: toward site-isolation of chromophores. J Am Chem Soc 122 (2000) 12385-12386
P Furuta, J Brooks, ME Thompson and JMJ Fréchet, Simultaneous light emission from a mixture of dendrimer encapsulated chromophores: a model for single-layer multichromophoric organic light-emitting diodes. J Am Chem Soc 125 (2003) 13165-13172
KM Gaab, AL Thompson, J Xu, TJ Martinez and CJ Bardeen, Meta-conjugation and excited-state coupling in phynylacetylene dendrimers. J Am Chem Soc 125 (2003) 9288-9289
TH Ghaddar, JF Wishard, DW Thompson, JK Whitesell and MA Fox, A Dendrimer-Based electron antenna: paired electron-transfer reactions in dendrimers with a 4,4′-bipyridine core and naphthalene peripheral groups. J Am Chem Soc 124 (2002) 8285-8289
SL Gilat, A Adronov and MJ Fréchet, Light harvesting and energy transfer in novel convergently constructed dendrimers. Angew Chem Int Ed 38 (1999) 1422-1427
R Gronheid, J Hofkens, F Kohn, T Weil, E Reuther, K Müllen and FC Schryer De, Intramolecular foster energy transfer in dendritic system at the single molecule level. J Am Chem Soc 124 (2002) 2418-2419
DM Guldi, A Swartz, C Luo, R Gomez, JL Segura and N Martin, Rigid dendritic donor-acceptor ensembles: control over energy and electron transduction. J Am Chem Soc 124 (2002) 10875-10886
D Gust, TA Moore and AL Moore, Molecular mimicry of photosynthetic energy and electron transfer. Acc Chem Res 26 (1993) 198-205
D Gust, TA Moore and AL Moore, Mimicking photosynthetic solar energy transduction. Acc Chem Res 34 (2001) 40-48
X Hu, A Damjanovic, T Ritz and K Schulten, Architecture and mechanism of the light-harvesting apparatus of purple bacteria. Proc Natl Acad Sci U.S.A 95 (1998) 5935-5941
DL Jiang, CK Choi, L Honda, WS Li, T Yuzawa and T Aida, Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes. J Am Chem Soc 126 (2004) 12084-12089
DL Jiang and T Aida, Morphology-dependent photochemical events in aryl ether dendrimer porphyrins: cooperation of dendron subunits for singlet energy transduction. J Am Chem Soc 120 (1998) 10895-10901
M Kawa and JMJ Fréchet, Self-assembled lanthanide-cored dendrimer complexes: enhancement of the luminescence properties of lanthanide ions through site-isolation and antenna effects. Chem Mater 10 (1998) 286-296
AL Lehninger, DL Nelson and MM. Cox, Principles of biochemistry. NewYork: Worth Publishers Inc (1993).
D Liu, S Feyter De, M Cotlet, A Stefan, U-M Wiesler, A Herrmann, D Grebel-Koehler, J Qu, K Müllen and FC Schryver De, Fluorescence and intramolecular energy transfer in polyphenylene dendrimers. Macromolecules 36 (2003) 5918-5925
M Maus, R De, M Lor, T Weil, S Mitra, U-M Wiesler, A Herrmann, J Hofkens, T Vosch, K Müllen and FC De Schryer, Intramolecular energy hopping and energy trapping in polyphenylene dendrimers with multiple peryleneimide. J Am Chem Soc 123 (2001) 7668-7676
G McDermott, SM Prince, AA Freer, AM Hawthrornthwaite-Lawless, MZ Papiz, RJ Cogdell and NW Isaacs, Crystal-Structure of an integral membrane light-harvesting complex from photosynthetic bacteria. Nature 374 (1995) 517-521
JS Melinger, Y Pan, VD Kleiman, Z Peng, BL Davis, D McMorrow and M Lu, Optical and photophysical properties of light-harvesting phenylacetylene monodendrons based on unsymmetrical branching. J Am Chem Soc 124 (2002) 12002-12012
Z Peng, Y Pan, B Xu and J Zhang, Synthesis and optical properties of novel unsymmetrical conjugated dendrimers. J Am Chem Soc 122 (2000) 6619-6623
Peng Z, Mellinger JS and Kleiman VD (2005) Personal Communication
J Qu, D Liu, S Feyter De, J Zhang, FC Schryver De and K Müllen, Synthesis and optical properties of polyphenylene dendrimers based on perylenes. J Org Chem 68 (2003) 9802-9808
J Qu, NG Pschirer, D Liu, A Stefan, FC Schryver De and K Müllen, Dendronized perylenetetracarboxdiimides with peripheral triphenylamines for intramolecular energy and electron transfer. Chem Eur J 10 (2004) 528-537
R Sadamoto, N Tomioka and T Aida, Photoinduced electron transfer reactions through dendrimer architecture. J Am Chem Soc 118 (1996) 3978-3979
Serin JM, Brousmiche W and Fréchet MT (2002) Cascade energy transfer in a conformationally mobile multichromophoric dendrimer. Chem Commun: 2605–2607
MR Shorteed, SF Swallen, Z-Y Shi, W Tan, Z Xu, C Devadoss, JS Moore and R Kopelman, Directed energy transfer in dendrimeric antenna supermolecules. J Phys Chem B 101 (1997) 6318-6322
GM Stewart and MA Fox, Chromophore-Labeled dendrons as light harvesting antennae. J Am Chem Soc 118 (1996) 4354-4360
KR Thomas, AL Thompson, AV Sivakumar, CJ Bardeen and S Thayumanavan, Energy and electron transfer in bifunctional non-conjugated dendrimers. J Am Chem Soc 127 (2005) 373-383
AL Thompson, KM Gaab, J Xu, CJ Bardeen and TJ Martinez, Variable Electronic Coupling in Phenylacetylene Dendrimers: The Role of Förster, Dexter and Charge-Transfer Interaction. J Phys Chem A 108 (2004) 671-682
Unpublished results from our laboratories
MR Wasielewski, Photoinduced electron transfer in supramolecular systems for artificial photosynthesis. Chem Rev 92 (1992) 435-461
SE Webber, Photon harvesting polymers. Chem Rev 90 (1990) 1469-1482
T Weil, E Reuther and K Müllen, Shape-Persistent, fluorescent polyphenylene dyads and a triad for efficient vectorial transduction of excitation energy. Angew Chem Int Ed 41 (2002) 1900-1904
T Weil, E Reuther, C Beer and K Müllen, Synthesis and characterization of dendritic multichromophores base on rylene dyes for vectorial transduction of excitation energy. Chem Eur J 10 (2004) 1398-1414
Z Xu and JS Moore, Rapid construction of large-size phenylacetylene dendrimers up to 12.5 nanometers in molecular diameter. Angew Chem Int Ed 32 (1993) 1354-1357
Xu, Design and synthesis of a convergent and directional molecular antenna. Acta Polym 45 (1994) 83-87
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nantalaksakul, A., Reddy, D.R., Bardeen, C.J. et al. Light Harvesting Dendrimers. Photosynth Res 87, 133–150 (2006). https://doi.org/10.1007/s11120-005-8387-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11120-005-8387-3