Pyrene-excimers-based antenna systems.

A series of dendrimeric compounds bearing pyrene units were synthesized to afford light-harvesting antennae based on the formation of intramolecular excimers. The synthetic plan profited from the efficiency of the Huisgen reaction, the 1,3-dipolar cycloaddition of azides and terminal alkynes, which allowed ready assembly of the different building blocks. The three molecular antennae obtained, of increasing generation, revealed efficient energy transfer both in solution and in the solid state.

[1]  Duong Tuan Quang,et al.  Calixarene-derived fluorescent probes. , 2007, Chemical reviews.

[2]  R. Métivier,et al.  Synthesis of bispyrenyl sugar-aza-crown ethers as new fluorescent molecular sensors for Cu(II). , 2007, The Journal of organic chemistry.

[3]  J. Moses,et al.  The growing applications of click chemistry. , 2007, Chemical Society reviews.

[4]  Yasuhiro Shiraishi,et al.  Effects of metal cation coordination on fluorescence properties of a diethylenetriamine bearing two end pyrene fragments. , 2007, The journal of physical chemistry. B.

[5]  Ó. Lopéz,et al.  Click Chemistry - What’s in a Name? Triazole Synthesis and Beyond , 2007 .

[6]  Anders Hult,et al.  A chemoselective approach for the accelerated synthesis of well-defined dendritic architectures. , 2007, Chemical communications.

[7]  Mercedes Crego-Calama,et al.  Design of fluorescent materials for chemical sensing. , 2007, Chemical Society reviews.

[8]  A. Harriman,et al.  Intramolecular excimer formation and delayed fluorescence in sterically constrained pyrene dimers. , 2007, Chemistry.

[9]  P. Foggi,et al.  The ultrafast energy transfer process in naphtole-nitrobenzofurazan bichromophoric molecular systems A study by femtosecond UV-vis pump-probe spectroscopy , 2007 .

[10]  Peng Wu,et al.  Catalytic Azide—Alkyne Cycloaddition: Reactivity and Applications , 2007 .

[11]  A. Harriman,et al.  Intramolecular Delayed Fluorescence as a Tool for Imaging Science: Synthesis and Photophysical Properties of a First-Generation Emitter , 2007 .

[12]  J. Lutz.  1,3‐Dipolare Cycloaddition von Aziden und Alkinen: eine universelle Ligationsmethode in den Polymer‐ und Materialwissenschaften , 2007 .

[13]  Jean-François Lutz,et al.  1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. , 2007, Angewandte Chemie.

[14]  Su Ho Kim,et al.  A PCT-based, pyrene-armed calix[4]crown fluoroionophore. , 2006, The Journal of organic chemistry.

[15]  Igor L. Medintz,et al.  Materials for fluorescence resonance energy transfer analysis: beyond traditional donor-acceptor combinations. , 2006, Angewandte Chemie.

[16]  Igor L. Medintz,et al.  Materialien für den resonanten Fluoreszenzenergietransfer (FRET): jenseits klassischer Donor‐Acceptor‐Kombinationen , 2006 .

[17]  Bernard Geffroy,et al.  Organic light‐emitting diode (OLED) technology: materials, devices and display technologies , 2006 .

[18]  Anne-Marie Caminade,et al.  Characterization of dendrimers. , 2005, Advanced drug delivery reviews.

[19]  C. Hawker,et al.  Structurally diverse dendritic libraries : A highly efficient functionalization approach using Click chemistry , 2005 .

[20]  A. L. Thompson,et al.  Energy and electron transfer in bifunctional non-conjugated dendrimers. , 2005, Journal of the American Chemical Society.

[21]  C. Botta,et al.  Organic Nanostructured Host–Guest Materials Containing Three Dyes , 2004 .

[22]  Ya‐Ping Sun,et al.  Functionalized Carbon Nanotubes with Tethered Pyrenes: Synthesis and Photophysical Properties , 2004 .

[23]  P. Prasad,et al.  Fluorescence resonance energy transfer in novel multiphoton absorbing dendritic structures , 2004 .

[24]  V. Balzani,et al.  Light-harvesting dendrimers. , 2003, Current opinion in chemical biology.

[25]  A. Juris.  6 Recent developments in photo- and redox-active dendrimers , 2003 .

[26]  G. D. Darling,et al.  Substituted 4-[4-(dimethylamino)styryl]pyridinium salt as a fluorescent probe for cell microviscosity. , 2003, Biosensors & bioelectronics.

[27]  Tobin J. Marks,et al.  Layer-by-Layer Self-Assembled Pyrrole-Based Donor-Acceptor Chromophores as Electro-Optic Materials , 2003 .

[28]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[29]  J. Fréchet,et al.  Femtosecond Transient Absorption Studies of Energy Transfer within Chromophore-Labeled Dendrimers , 2001 .

[30]  Jean M. J. Fréchet,et al.  Light-harvesting dendrimers , 2000 .

[31]  J. Fréchet,et al.  Dendrimer-Containing Light-Emitting Diodes: Toward Site-Isolation of Chromophores , 2000 .

[32]  L. A. Baker,et al.  Photophysical Properties of Pyrene-Functionalized Poly(propylene imine) Dendrimers , 2000 .

[33]  M. Shimomura,et al.  New Fluorimetric Alkali and Alkaline Earth Metal Cation Sensors Based on Noncyclic Crown Ethers by Means of Intramolecular Excimer Formation of Pyrene , 1998 .

[34]  T. Sakurai,et al.  Synthesis and Complexation Behavior of Diaza-18-crown-6 Carrying Two Pyrenylmethyl Groups. , 1997 .

[35]  Raoul Kopelman,et al.  Dendrimers as Controlled Artificial Energy Antennae , 1997 .

[36]  Shammai Speiser,et al.  Photophysics and Mechanisms of Intramolecular Electronic Energy Transfer in Bichromophoric Molecular Systems: Solution and Supersonic Jet Studies. , 1996, Chemical reviews.

[37]  M. Fox,et al.  Chromophore-Labeled Dendrons as Light Harvesting Antennae , 1996 .

[38]  J. Desvergne,et al.  A COOPERATIVE EFFECT IN SODIUM CATION COMPLEXATION BY A MACROCYCLIC BIS(9,10)ANTHRACENO-CROWN ETHER IN THE GROUND STATE AND IN THE EXCITED STATE , 1994 .

[39]  F. Winnik.  PHOTOPHYSICS OF PREASSOCIATED PYRENES IN AQUEOUS POLYMER SOLUTIONS AND IN OTHER ORGANIZED MEDIA , 1993 .

[40]  G. Duveneck,et al.  Intramolecular excimer formation with 1,3-di(1-pyrenyl)propane. Decay parameters and influence of viscosity , 1984 .

[41]  I. H. Munro,et al.  'Excimer’ fluorescence II. Lifetime studies of pyrene solutions , 1963, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[42]  Ya‐Ping Sun,et al.  Excited-state energy transfers in single-walled carbon nanotubes functionalized with tethered pyrenes , 2007 .

[43]  H. Hiemstra,et al.  CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective , 2005 .

[44]  C. Saudan,et al.  Luminescent dendrimers. Recent advances. , 2003, Topics in current chemistry.

[45]  J. Williams,et al.  Luminescence behaviour of cadmium, lead, zinc, copper, nickel and lanthanide complexes of octadentate macrocyclic ligands bearing naphthyl chromophores , 1995 .

[46]  K. Ichikawa,et al.  A fluorescent calix[4]arene as an intramolecular excimer-forming Na+ sensor in nonaqueous solution , 1992 .

[47]  S. Shinkai,et al.  Fluorescent calix[4]arene which responds to solvent polarity and metal ions , 1991 .

[48]  M. van der Auweraer,et al.  Intramolecular excimer formation in bichromophoric molecules linked by a short flexible chain , 1987 .

[49]  A. Castellan,et al.  Cation-directed photochemistry of an anthraceno-crown ether , 1986 .

[50]  T. Főrster,et al.  10th Spiers Memorial Lecture. Transfer mechanisms of electronic excitation , 1959 .