Syntheses and applications of furanyl-functionalised 2,2’:6’,2’’-terpyridines

Different synthetic routes leading to terpyridines functionalised with furan heterocycles are reviewed. The methodologies used to prepare such compounds include the ring closure of 1,5-diketones and cross-coupling reactions. These versatile terpyridines and their derived metal complexes find applications in various fields including coordination chemistry, medicinal chemistry and material sciences.

[1]  M. Knorr,et al.  2,2′:6′,2″‐Terpyridines Functionalized with Thienyl Substituents: Synthesis and Applications , 2012 .

[2]  L. Guyard,et al.  A more efficient synthesis of 4,4′,4′′-tricarboxy-2,2′:6′,2′′-terpyridine , 2011 .

[3]  Misaki Nakai,et al.  Synthesis and characterization of novel cyclometalated iridium(III) complexes for nanocrystalline TiO2-based dye-sensitized solar cells , 2011 .

[4]  Amlan K. Pal,et al.  Discrete covalent organic-inorganic hybrids: terpyridine functionalized polyoxometalates obtained by a modular strategy and their metal complexation. , 2011, Inorganic chemistry.

[5]  G. Zeni,et al.  New development of synthesis and reactivity of seleno- and tellurophenes. , 2011, Organic & biomolecular chemistry.

[6]  Claire H. Woo,et al.  Incorporation of furan into low band-gap polymers for efficient solar cells. , 2010, Journal of the American Chemical Society.

[7]  Yunhui Li,et al.  Studies of an Extremely High Molar Extinction Coefficient Ruthenium Sensitizer in Dye-Sensitized Solar Cells , 2010 .

[8]  J. Hihn,et al.  Effects of polypyrrole modified electrode functionalization on potentiometric pH responses , 2010 .

[9]  Anders Hagfeldt,et al.  Dye-sensitized solar cells. , 2010, Chemical reviews.

[10]  C. Bignozzi,et al.  Combination of cobalt and iron polypyridine complexes for improving the charge separation and collection in Ru(terpyridine)(2)-sensitised solar cells. , 2010, Chemistry.

[11]  Kiyoshi C. D. Robson,et al.  Systematic manipulation of the light-harvesting properties for tridentate cyclometalated ruthenium(II) complexes. , 2009, Inorganic chemistry.

[12]  J. Schneider,et al.  Platinum(II) terpyridyl acetylide complexes on platinized TiO(2): toward the photogeneration of H(2) in aqueous media. , 2009, Inorganic chemistry.

[13]  G. Shi,et al.  Conducting polymer nanomaterials: electrosynthesis and applications. , 2009, Chemical Society reviews.

[14]  Marie-Pierre Santoni,et al.  A divergent strategy for covalently-tethered (tpy)2Ru(II) systems based on Rh2(N,N'-diphenylbenzamidinates)4. , 2009, Dalton transactions.

[15]  Marie-Pierre Santoni,et al.  Spanning pairs of Rh2(acetate)4 units with Ru(II) complexes. , 2008, Inorganic chemistry.

[16]  G. Hanan,et al.  Carboxy-derived (tpy)2Ru2+ complexes as sub-units in supramolecular architectures: The solubilized ligand 4′-(4-carboxyphenyl)-4,4″-di-(tert-butyl)tpy and its homoleptic Ru(II) complex , 2008 .

[17]  S. Balasubramanian,et al.  Synthesis, characterization and electrochemistry of 4'-functionalized 2,2':6',2''-terpyridine ruthenium(II) complexes and their biological activity. , 2008, Dalton transactions.

[18]  Silvia Schaffner,et al.  Expanded ligands: bis(2,2':6',2''-terpyridine carboxylic acid)ruthenium(ii) complexes as metallosupramolecular analogues of dicarboxylic acids. , 2007, Dalton transactions.

[19]  P. Merino,et al.  Furan Oxidations in Organic Synthesis: Recent Advances and Applications , 2007 .

[20]  Guo-Li Shen,et al.  Synthesis of porphyrin-appended terpyridine as a chemosensor for cadmium based on fluorescent enhancement. , 2007, Talanta.

[21]  F. Krebs,et al.  Characterisation and application of new carboxylic acid-functionalised ruthenium complexes as dye-sensitisers for solar cells , 2007 .

[22]  V. Sundström,et al.  Synthesis and electron transfer studies of ruthenium-terpyridine-based dyads attached to nanostructured TiO2. , 2007, Inorganic chemistry.

[23]  U. Schubert,et al.  Modern Terpyridine Chemistry , 2006 .

[24]  Ulrich S. Schubert,et al.  Modern Terpyridine Chemistry: SCHUBERT: MODERN TERPYRIDINE CHEMISTRY O-BK , 2006 .

[25]  U. Flörke,et al.  A Versatile Domino Synthesis Affording Novel S- and U-Shaped Terpyridines. – Synthesis, Properties and Crystal Structure , 2006 .

[26]  J. Petit,et al.  Preparation and properties of ruthenium (II) complexes of 2,2′:6′,2″-terpyridines substituted at the 4′-position with heterocyclic groups , 2005 .

[27]  Pablo Espinet,et al.  The mechanisms of the Stille reaction. , 2004, Angewandte Chemie.

[28]  N. M. Iha,et al.  Metal complex sensitizers in dye-sensitized solar cells , 2004 .

[29]  A. Winter,et al.  Selective synthesis of U-shaped terpyridines. Versatile ligands for the preparation of platinum complexes. , 2004, Organic & biomolecular chemistry.

[30]  G. Kirsch,et al.  Synthesis of New Terpyridines under Solventless Conditions Using Alumina , 2004 .

[31]  M. Grätzel.  Dye-sensitized solar cells , 2003 .

[32]  G. Kirsch,et al.  A novel pathway for the synthesis of a carboxylic acid-functionalised Ru(II) terpyridine complex , 2003 .

[33]  U. Schubert,et al.  Functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines via stille-type cross-coupling procedures. , 2002, The Journal of organic chemistry.

[34]  T. R. Kelly,et al.  Synthesis of some unsymmetrical bridged terpyridines. , 2002, The Journal of organic chemistry.

[35]  C. Raston,et al.  Efficient synthesis of pyridines via a sequential solventless aldol condensation and Michael addition , 2001 .

[36]  Gareth W. V. Cave,et al.  Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. , 2001, Chemical communications.

[37]  T. Jeong,et al.  Synthesis, topoisomerase I inhibition and antitumor cytotoxicity of 2,2':6',2"-, 2,2':6',3"- and 2,2':6',4"-terpyridine derivatives. , 2001, Bioorganic & medicinal chemistry letters.

[38]  C. Bignozzi,et al.  New ruthenium bisterpyridinyl complexes, as efficient sensitizers of nanocrystalline, TiO2 films , 2001 .

[39]  G. Chelucci,et al.  New chiral 2,2′:6′,2″-terpyridines as ligands for asymmetric catalysis: cyclopropanation and hydrosilylation reactions , 2001 .

[40]  Ziessel,et al.  Facile synthesis of polypyridine esters: A route to functionalized aldehydes , 2000, The Journal of organic chemistry.

[41]  G. Kirsch,et al.  On the way to unsymmetrical terpyridines carrying carboxylic acids , 2000 .

[42]  Michael Grätzel,et al.  Applications of functionalized transition metal complexes in photonic and optoelectronic devices , 1998 .

[43]  N. Risch,et al.  Application of iminium salts in the synthesis of fused pyridines. Introduction of substituents using ternary iminium perchlorates , 1993 .

[44]  J. Roncali.  Conjugated poly(thiophenes): synthesis, functionalization, and applications , 1992 .

[45]  K. T. Potts,et al.  Synthesis of 4'-vinyl-2,2':6'2″-terpyridine , 1991 .

[46]  Hsien-Hsin Chou,et al.  Organic dyes containing furan moiety for high-performance dye-sensitized solar cells. , 2009, Organic letters.

[47]  M. Beley,et al.  Preparation and study of ruthenium(II) 2,2′:6′,2″-terpyridine complexes linked by an O–CH2 spacer to thiophene moieties , 2006 .

[48]  Ge Wang.  which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Fractal MapReduce decomposition of sequence alignment , 2005 .

[49]  G. Hanan,et al.  A Facile Route to Sterically Hindered and Non-Hindered 4′-Aryl-2,2′:6′,2′′-Terpyridines , 2005 .

[50]  Marek P. Krzemiński,et al.  The Cross-Coupling Reaction , 2005 .

[51]  N. Miyaura.  Cross-Coupling Reactions , 2002 .

[52]  Gareth W. V. Cave,et al.  Toward benign syntheses of pyridines involving sequential solvent free aldol and Michael addition reactions , 2000 .

[53]  R. Fallahpour.  Carboxylate Derivatives of Oligopyridines , 2000 .

[54]  B. Ranu,et al.  Surface-mediated solid phase reaction: dramatic improvement of Michael reaction on the surface of alumina , 1992 .

[55]  A. García-Raso,et al.  An Improved Procedure for the Michael Reaction of Chalcones , 1982 .

[56]  F. Kröhnke.  The Specific Synthesis of Pyridines and Oligopyridines1 , 1976 .

[57]  F. H. Burstall,et al.  347. Researches on residual affinity and co-ordination. Part XXXVII. Complex metallic salts containing 2 : 6-di-2′-pyridylpyridine (2 : 2′ : 2″-tripyridyl) , 1937 .

[58]  F. H. Burstall,et al.  3. Dehydrogenation of pyridine by anhydrous ferric chloride , 1932 .