Abstract
Dendrimers are well-defined tree-like macromolecules possessing numerous chain ends emanating from a single core, which makes them attractive candidates for mimicking light-harvesting systems and hydrogenases. Photoinduced electron and energy transfers are main processes involved in light-harvesting and photocatalysis. In this article, the general concepts of design strategies and recent developments of photofunctional dendrimers in biomimics of light-harvesting systems and hydrogenases are discussed. The energy transfer and electron transfer processes in light-harvesting dendrimers and the effect of dendritic structures in photochemical hydrogen production are illustrated.
Similar content being viewed by others
References
Hu XC, Damjanovic A, Ritz T, Schulten K. Architecture and mechanism of the light-harvesting apparatus of purple bacteria. Proc Natl Acad Sci USA, 1998, 95: 5935–5941
Andreiadis ES, Chavarot-Kerlidou M, Fontecave M, Artero V. Artificial photosynthesis: from molecular catalysts for light-driven water splitting to photoelectrochemical cells. Photochem Photobiol, 2011, 87: 946–964
Feng J, Wang Q, Zhang XJ, Huang YG, Ai XC, Zhang XJ, Zhang JP. Spectroscopic evidence for triplet energy transfer among carotinoids in the LH2 complex from photosynthesis bacterium Rhodopseudomonas palustris. Sci China Ser B, 2004, 47: 80–90
Thoi VS, Sun YJ, Long JR, Chang CJ. Complexes of earth-abundant metals for catalytic electrochemical hydrogen generation under aqueous conditions. Chem Soc Rev, 2013, 42: 2388–2400
Frischmann PD, Mahata K, Wuerthner F. Powering the future of molecular artificial photosynthesis with light-harvesting metallosupramolecular dye assemblies. Chem Soc Rev, 2013, 42: 1847–1870
Mcdermott G, Prince SM, Freer AA, Hawthornthwaitelawless AM, Papiz MZ, Cogdell RJ, Isaacs NW. Crystal-structure of an integral membrane light-harvesting complex from photosynthetic bacteria. Nature, 1995, 374: 517–521
Jiang DL, Aida T. Bioinspired molecular design of functional dendrimers. Prog Polym Sci, 2005, 30: 403–422
Liang C, Frechet JMJ. Applying key concepts from nature: transition state stabilization, pre-concentration and cooperativity effects in dendritic biomimetics. Prog Polym Sci, 2005, 30, 385–402
Jang WD, Selim KMK, Lee CH, Kang IK. Bioinspired application of dendrimers: from bio-mimicry to biomedical applications. Prog Polym Sci, 2009, 34: 1–23
Cheng YC, Fleming GR. Dynamics of light harvesting in photosynthesis. Annu Rev Phys Chem, 2009, 60: 241–262
Scholes GD, Fleming GR, Olaya-Castro A, van Grondelle R. Lessons from nature about solar light harvesting. Nat Chem, 2011, 3: 763–774
Frischmann PD, Mahata K, Würthner F. Powering the future of molecular artificial photosynthesis with light-harvesting metallosupramolecular dye assemblies. Chem Soc Rev, 2013, 42: 1847–1870
Wasielewski MR. Self-assembly strategies for integrating light harvesting and charge separation in artificial photosynthetic systems. Acc Chem Res, 2009, 42: 1910–1921
Ajayaghosh A, Praveen AK, Vijayakuma C. Organogels as scaffolds for excitation energy transfer and light harvesting. Chem Soc Rev, 2008, 37: 109–122
Albinsson B, Hannestad JK, Börjesson K. Functionalized DNA nanostructures for light harvesting and charge separation. Coordin Chem Rev, 2012, 256: 2399–2413
Zeng Y, Li YY, Chen JP, Yang GQ, Li Y. Dendrimers: a mimic natural light-harvesting system. Chem Asian J, 2010, 5: 992–1005
Adronov A, Fréchet JMJ. Light-harvesting dendrimers. Chem Commun, 2000: 1701–1710
Balzani V, Ceroni P, Maestri M, Vicinelli V. Light-harvesting dendrimers. Curr Opin Chem Biol, 2003, 7: 657–665
Astruc D, Boisselier E, Ornelas C. Dendrimers designed for functions: from physical, photophysical, and supramolecular properties to applications in sensing, catalysis, molecular electronics, photonics, and nanomedicine. Chem Rev, 2010, 110: 1857–1959
Förster T. Zwischenmolekulare energiewanderung und fluoreszenz. Ann Phys, 1948, 2: 55–75
Dexter DL. A theory of sensitized luminescence in solids. J Chem Phys, 1953, 21: 836–850
Katz JL, Choi S, Jortner J, Rice SA. Triplet exciton bands in aromatic crystals. J Chem Phys, 1963, 39: 1897–1899
Denti G, Campagna S, Serroni S, Ciano M, Balzani V. Decanuclear homo- and heterometallic polypyridine complexes: syntheses, absorption spectra, luminescence, electrochemical oxidation, and intercomponent energy transfer. J Am Chem Soc, 1992, 114: 2944–2950
Xu ZF, Moore JS. Rapid construction of large-size phenylacetylene dendrimers up to 12.5 nanometers in molecular diameter. Angew Chem Int Ed, 1993, 32: 1354–1357
Melinger JS, Pan YC, Kleiman VD, Peng ZH, Davis BL, McMorrow D, Lu M. Optical and photophysical properties of light-harvesting phenylacetylene monodendrons based on unsymmetrical branching. J Am Chem Soc, 2002, 124: 12002–12012
Atas E, Peng ZH, Kleiman VD. Energy transfer in unsymmetrical phenylene ethynylene dendrimers. J Phys Chem B, 2005, 109: 13553–13560
Kuroda DG, Singh CP, Peng ZH, Kleiman VD. Mapping excited-state dynamics by coherent control of a dendrimer’s photoemission efficiency. Science, 2009, 326: 263–267
Adronov A, Gilat SL, Fréchet JMJ, Ohta K, Neuwahl FVR, Fleming GR. Light harvesting and energy transfer in laser-dye-labeled poly(aryl ether) dendrimers. J Am Chem Soc, 2000, 122: 1175–1185
Bergamini G, Ceroni P, Maestri M, Balzani V, Lee SK, Vogtle F. Forward (singlet-singlet) and backward (triplet-triplet) energy transfer in a dendrimer with peripheral naphthalene units and a benzophenone core. Photochem Photobiol Sci, 2004, 3: 898–905
Giansante C, Ceroni P, Balzani V, Maestri M, Lee SK, Vogtle F. Photophysical, photochemical, and electrochemical properties of dendrimers with a dimethoxybenzil core. New J Chem, 2007, 31: 1250–1258
Chen JP, Li SY, Zhang L, Liu BN, Han YB, Yang GQ, Li Y. Light-harvesting and photoisomerization in benzophenone and norbornadiene-labeled poly(aryl ether) dendrimers via intramolecular triplet energy transfer. J Am Chem Soc, 2005, 127: 2165–2171
Chen JP, Li SY, Zhang L, Li YY, Chen J, Yang GQ, Li Y. Direct observation of the intramolecular triplet-triplet energy transfer in poly(aryl ether) dendrimers. J Phys Chem B, 2006, 110: 4047–4053
Zhang L, Chen JP, Li SY, Chen J, Li YY, Yang GQ, Li Y. 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 Photochem Photobiol A, 2006, 181: 429–436
Rehm D, Weller A. Kinetics of fluorescence quenching by electron and H-atom transfer. Isr J Chem, 1970, 8: 259–271
Stewart GM, Fox MA. Chromophore-labeled dendrons as light harvesting antennae. J Am Chem Soc, 1996, 118: 4354–4360
Ghaddar TH, Wishart JF, Thompson DW, Whitesell JK, Fox MA. 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, 2002, 124: 8285–8289
Guldi DM, Swartz A, Luo C, GĂłmez R, Segura JL, MartĂn N. Rigid dendritic donor-acceptor ensembles: control over energy and electron transduction. J Am Chem Soc, 2002, 124: 10875–10886
Qu JQ, Pschirer NG, Liu DJ, Stefan A, De Schryver FC, Mullen K. Dendronized perylenetetracarboxdiimides with peripheral triphenylamines for intramolecular energy and electron transfer. Chem Eur J, 2004, 10: 528–537
Thomas KRJ, Thompson AL, Sivakumar AV, Bardeen CJ, Thayumanavan S. Energy and electron transfer in bifunctional non-conjugated dendrimers. J Am Chem Soc, 2005, 127: 373–383
Chen J, Chen JP, Li SY, Zhang L, Yang GQ, Li Y. Conversion of intramolecular singlet electron transfer at room temperature into triplet energy transfer at 77 K: photoisomerization in norbornadiene- and carbazole-labeled poly(aryl ether) dendrimers. J Phys Chem B, 2006, 110: 4663–4670
Chen JP, Zhang L, Li SY, Li YY, Chen J, Yang GQ, Li Y. Valence isomerization in dendrimers by photo-induced electron transfer and energy transfer from the dendrimer backbone to the core. J Photochem Photobiol A, 2007, 185: 67–75.
Li YY, Han L, Chen JP, Zheng SJ, Zen Y, Li Y, Li SY, Yang GQ. Study on the extent of folding back conformation in poly(aryl ether) dendrimers by intramolecular electron transfer and exciplex formation. Macromolecules, 2007, 40: 9384–9390
Li M, Li YY, Zeng Y, Chen JP, Li Y. Intramolecular exciplex formation induced by the folding-back conformation of poly(aryl ether) dendrimers. J Phys Chem C, 2009, 113: 11554–11559
Schenning APHJ, Peeters E, Meijer EW. Energy transfer in supramolecular assemblies of oligo(p-phenylene vinylene)s terminated poly(propylene imine) dendrimers. J Am Chem Soc, 2000, 122: 4489–4495
Hahn U, Gorka M, Vogtle F, Vicinelli V, Ceroni P, Maestri M, Balzani V. Light-harvesting dendrimers: efficient intra- and intermolecular energy-transfer processes in a species containing 65 chromophoric groups of four different types. Angew Chem Int Ed, 2002, 41: 3595–3598
Balzani V, Bergamini G, Ceroni P, Marchi E. Designing light harvesting antennas by luminescent dendrimers. New J Chem, 2011, 35: 1944–1954
Giansante C, Ceroni P, Balzani V, Voegtle F. Self-assembly of a light-harvesting antenna formed by a dendrimer, a Ru-II complex, and a Nd-III ion. Angew Chem Int Ed, 2008, 47: 5422–5425
Branchi B, Ceroni P, Balzani V, Bergamini G, Klaerner FG, Voegtle F. Adducts between dansylated poly(propylene amine) dendrimers and anthracene clips mediated by Zn-II ions: highly efficient photoinduced energy transfer. Chem Eur J, 2009, 15: 7876–7882
Marchi E, Baroncini M, Bergamini G, Van Heyst J, Voegtle F, Ceroni P. Photoswitchable metal coordinating tweezers operated by light-harvesting dendrimers. J Am Chem Soc, 2012, 134: 15277–15280
Pillai ZS, Ceroni P, Kubeil M, Heldt JM, Stephan H, Bergamini G. Dendrimers as Nd3+ ligands: effect of generation on the efficiency of the sensitized Lanthanide emission. Chem Asian J, 2013, 8: 771–777
De Schryver FC, Vosch T, Cotlet M, Van der Auweraer M, Mullen K, Hofkens J. Energy dissipation in multichromophoric single dendrimers. Acc Chem Res, 2005, 38: 514–522
Weil T, Reuther E, Müllen K. Shape-persistent, fluorescent polyphenylene dyads and a triad for efficient vectorial transduction of excitation energy. Angew Chem Int Ed, 2002, 41: 1900–1904
Serin JM, Brousmiche DW, Fréchet JMJ. Cascade energy transfer in a conformationally mobile multichromophoric dendrimer. Chem Commun, 2002, 2605–2607
Zhang J, Fischer MKR, Baeuerle P, Goodson TIII. Energy migration in dendritic oligothiophene-perylene bisimides. J Phys Chem B, 2013, 117: 4204–4215
Zeng Y, Li YY, Li M, Yang GQ, Li Y. Enhancement of energy utilization in light-harvesting dendrimers by the pseudorotaxane formation at periphery. J Am Chem Soc, 2009, 131: 9100–9106
Hu Rr, Leung NLC, Tang BZ. AIE macromolecules: syntheses, structures and functionalities. Chem Soc Rev, 2014, 43: 4494–4562
Zeng Y, Li P, Liu XY, Yu YJ, Chen JP, Yang GQ, Li Y. A “breathing” dendritic molecule-conformational fluctuation induced by external stimuli. Polym Chem, 2014, 5: 5978–5984
Ghirardi ML, Dubini A, Yu JP, Maness PC. Photobiological hydrogen-producing systems. Chem Soc Rev, 2009, 38: 52–61
Fontecilla-Camps JC, Amara P, Cavazza C, Nicolet Y, Volbeda A. Structure-function relationships of anaerobic gas-processing metalloenzymes. Nature, 2009, 460: 814–822
Wang W, Yu TJ, Zeng Y, Chen JP, Yang GQ and Li Y. Enhanced photocatalytic hydrogen production from an MCM-41-immobilized photosensitizer-[Fe-Fe] hydrogenase mimic dyad. Photochem Photobiol Sci, 2014, 13: 1590–1597
Sakamoto M, Kamachi T, Okura I, Ueno A, Mihara H. Photoinduced hydrogen evolution with peptide dendrimer-multi-Zn(II)-porphyrin, viologen, and hydrogenase. Biopolymers, 2001, 59: 103–109
Jiang DL, Choi CK, Honda K, Li WS, Yuzawa T, Aida T. Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes. J Am Chem Soc, 2004, 126: 12084–12089
Yu TJ, Wang W, Chen JP, Zeng Y, Li YY, Yang GQ, Li Y. Dendrimer-encapsulated Pt nanoparticles: an artificial enzyme for hydrogen production. J Phys Chem C, 2012, 116: 10516–10521
Ravotto L, Mazzaro R, Natali M, Ortolani L, Morandi V, Ceroni P, Bergamini G. Photoactive dendrimer for water photoreduction: a scaffold to combine sensitizers and catalysts. J Phys Chem Lett, 2014, 5: 798–803
Yu TJ, Zeng Y, Chen JP, Li YY, Yang GQ, Li Y. Exceptional dendrimer-based mimics of diiron hydrogenase for the photochemical production of hydrogen. Angew Chem Int Ed, 2013, 52: 5631–5635
Collini E, Scholes GD. Coherent intrachain energy migration in a conjugated polymer at room temperature. Science, 2009, 323: 369–373
Collini E, Wong CY, Wilk KE, Curmi PMG, Brumer P, Scholes GD. Coherently wired light-harvesting in photosynthetic marine algae at ambient temperature. Nature, 2010, 463: 644–647
Olaya-Castro A, Scholes GD. Energy transfer from Forster-Dexter theory to quantum coherent light-harvesting. Int Rev Phys Chem, 2011, 30: 49–77
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Liu, X., Zeng, Y., Zhang, X. et al. Dendrimers-merging biomimics and photoenergy conversion. Sci. China Chem. 58, 390–399 (2015). https://doi.org/10.1007/s11426-014-5293-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-014-5293-6