Azido- and Ethynyl-Substituted
2,2′:6′,2′′-Terpyridines as
Suitable Substrates for Click Reactions

Andreas Winter; Andreas Wild; Richard Hoogenboom; Martin W. M. Fijten; Martin D. Hager; Reza-Ali Fallahpour; Ulrich S. Schubert

doi:10.1055/s-0028-1088159

PAPER

Azido- and Ethynyl-Substituted 2,2′:6′,2′′-Terpyridines as Suitable Substrates for Click Reactions

Andreas Winter^a, Andreas Wild^b, Richard Hoogenboom^a, Martin W. M. Fijten^a, Martin D. Hager^b, Reza-Ali Fallahpour^c, Ulrich S. Schubert*^a,b
^a Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands
Fax: +31(40)2474186; e-Mail: u.s.schubert@tue.nl;
^b Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
^c HetCat, Gundeldingerstr. 174, 4053 Basel, Switzerland

Abstract

All articles of this category

Abstract

The click reaction of azido- and ethynyl-functionalized terpyridines has been exploited to obtain a series of 1H-1,2,3-triazole-substituted terpyridines. This protocol was extended towards the synthesis of terpyridine-based macroligands via end group modification of ethynyl-functionalized polymers. Finally, the combination of two orthogonal terpyridines within one click reaction highlights the potential of this approach with respect to the preparation of new building blocks for supramolecular assemblies and functional materials.

Key words

click reaction - complexes - cycloaddition - ligands - terpyridines

Full Text

References

<A NAME="RT16708SS-1A">1a</A> Schubert US. Hofmeier H. Newkome GR. Modern Terpyridine Chemistry Wiley-VCH; Weinheim: 2006.

<A NAME="RT16708SS-1B">1b</A> Newkome GR. Wang P. Moorefield CN. Cho TJ. Mohoapatra PP. Li S. Hwang S.-H. Lukoyanova O. Echegoyen L. Palagallo JA. Lancu V. Hla S.-W. Science 2006, 312: 1782

<A NAME="RT16708SS-1C">1c</A> Bonnet S. Collin J.-P. Koizumi M. Mobian P. Sauvage J.-P. Adv. Mater. (Weinheim, Ger.) 2006, 18: 1239

<A NAME="RT16708SS-1D">1d</A> Brunsveld L. Folmer BJB. Sijbesma RP. Meijer EW. Chem. Rev. 2001, 101: 4071

<A NAME="RT16708SS-2A">2a</A> Lohmeijer BGG. Schubert US. Macromol. Chem. Phys. 2003, 204: 1072

<A NAME="RT16708SS-2B">2b</A> Yuan YC. Yin T. Rong MZ. Zhang MQ. eXPRESS Polym. Lett. 2008, 2: 238

<A NAME="RT16708SS-2C">2c</A> Bergman SD. Wudl F. J. Mater. Chem. 2008, 18: 41

<A NAME="RT16708SS-3A">3a</A> Constable EC. Adv. Inorg. Chem. Radiochem. 1986, 30: 69

<A NAME="RT16708SS-3B">3b</A> Schubert US. Eschbaumer C. Andres P. Hofmeier H. Weidl HC. Herdtweck E. Dulkeith E. Morteani A. Hecker NE. Feldmann J. Synth. Met. 2001, 121: 1249

<A NAME="RT16708SS-4A">4a</A> Erkkila KE. Odom DT. Barton JK. Chem. Rev. 1999, 99: 2777

<A NAME="RT16708SS-4B">4b</A> Barigeletti F. Flamigni L. Chem. Soc. Rev. 2000, 29: 1

<A NAME="RT16708SS-4C">4c</A> Andres PR. Schubert US. Adv. Mater. (Weinheim, Ger.) 2004, 16: 1043

<A NAME="RT16708SS-4D">4d</A> Hofmeier H. Schubert US. Chem. Soc. Rev. 2004, 33: 373

<A NAME="RT16708SS-4E">4e</A> Schmittel M. Kalsani V. Mal P. Bats JW. Inorg. Chem. 2006, 45: 6370

<A NAME="RT16708SS-4F">4f</A> Hwang SH. Moorefield CN. Dai L. Newkome GR. Chem. Mater. 2006, 18: 4019

<A NAME="RT16708SS-5A">5a</A> Ziessel R. Hissler M. El-ghayoury A. Harriman A. Coord. Chem. Rev. 1998, 178-180: 1251

<A NAME="RT16708SS-5B">5b</A> Balzani V. Ceroni P. Juris A. Venturi A. Venturi M. Campagna S. Puntoriero F. Serroni S. Coord. Chem. Rev. 2001, 219-221: 545

<A NAME="RT16708SS-5C">5c</A> Flood AH. Stoddart JF. Steuerman DW. Heath JR. Science 2004, 306: 2055

<A NAME="RT16708SS-5D">5d</A> Ciofini I. Lainé PP. Bedioui F. Adamo C. J. Am. Chem. Soc. 2004, 126: 10763

<A NAME="RT16708SS-5E">5e</A> Duprez V. Biancardo M. Spanggaard H. Krebs FC. Macromolecules 2005, 38: 10436

<A NAME="RT16708SS-5F">5f</A> Benniston A. Harriman A. Li P. Patel PV. Sams CA. J. Org. Chem. 2006, 71: 3481

<A NAME="RT16708SS-6A">6a</A> Hofmeier H. Hoogenboom R. Wouters MEL. Schubert US. J. Am. Chem. Soc. 2005, 127: 2913

<A NAME="RT16708SS-6B">6b</A> Lohmeijer BGG. Schubert US. Angew. Chem. Int. Ed. 2002, 41: 3825

<A NAME="RT16708SS-6C">6c</A> Lohmeijer BGG. Schubert US. J. Polym. Sci., Part A: Polym. Chem. 2004, 42: 4016

<A NAME="RT16708SS-6D">6d</A> Schmatloch S. van den Berg AMJ. Alexeev AS. Hofmeier H. Schubert US. Macromolecules 2003, 36: 9943

<A NAME="RT16708SS-6E">6e</A> Meier MAR. Lohmeijer BGG. Schubert US. Macromol. Rapid Commun. 2003, 24: 852

<A NAME="RT16708SS-6F">6f</A> Winter A. Schubert US. Macromol. Chem. Phys. 2007, 208: 1956

<A NAME="RT16708SS-7A">7a</A> Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

<A NAME="RT16708SS-7B">7b</A> Chan TR. Hilgraf R. Sharpless KB. Fokin VV. Org. Lett. 2004, 6: 2853

<A NAME="RT16708SS-7C">7c</A> Huisgen R. Szeimies G. Möbius L. Chem. Ber. 1967, 100: 2494

<A NAME="RT16708SS-7D">7d</A> Huisgen R. Knorr R. Möbius L. Szeimies G. Chem. Ber. 1965, 98: 4014

<A NAME="RT16708SS-7E">7e</A> Boyer JH. Hamer J. J. Am. Chem. Soc. 1955, 77: 951

<A NAME="RT16708SS-8">8</A> Fournier D. Hoogenboom R. Schubert US. Chem. Soc. Rev. 2007, 36: 1369

<A NAME="RT16708SS-9A">9a</A> Haensch C. Hoeppener S. Schubert US. Nanotechnology 2008, 19: 035703

<A NAME="RT16708SS-9B">9b</A> Sommer WJ. Weck M. Langmuir 2007, 23: 11991

<A NAME="RT16708SS-9C">9c</A> Nandivada H. Jiang X. Lahann J. Adv. Mater. (Weinheim, Ger.) 2007, 19: 2197

<A NAME="RT16708SS-9D">9d</A> Devaraj NK. Collman JP. QSAR Comb. Sci. 2007, 26: 1253

<A NAME="RT16708SS-10A">10a</A> Hawker CJ. Wooley KL. Science 2005, 309: 1200

<A NAME="RT16708SS-10B">10b</A> Aucagne V. Hanni KD. Leigh AD. Lusby PJ. Walker DB. J. Am. Chem. Soc. 2006, 128: 2186

<A NAME="RT16708SS-10C">10c</A> Dichtel WR. Miljanic OS. Spruell JM. Heath JR. Stoddart JF. J. Am. Chem. Soc. 2006, 128: 10388

<A NAME="RT16708SS-10D">10d</A> Mobian P. Collin J.-P. Sauvage J.-P. Tetrahedron Lett. 2006, 47: 4907

<A NAME="RT16708SS-10E">10e</A> Devaraj NK. Dinolfo PH. Chidsey CED. Collman JP. J. Am. Chem. Soc. 2006, 128: 1794

<A NAME="RT16708SS-10F">10f</A> Wu P. Fokin VV. Aldrichimica Acta 2007, 40: 7

<A NAME="RT16708SS-10G">10g</A> Monkowius U. Ritter S. König B. Zabel M. Yersin H. Eur. J. Inorg. Chem. 2007, 29: 4597

<A NAME="RT16708SS-10H">10h</A> David O. Maisonneuve S. Xie J. Tetrahedron Lett. 2007, 48: 6527

<A NAME="RT16708SS-11">11</A> Fallahpour R.-A. Neuburger M. Zehnder M. Synthesis 1999, 1051

<A NAME="RT16708SS-12A">12a</A> Tomalia DA. Sheetz DP. J. Polym. Sci., Part A: Polym. Chem. 1966, 4: 2253

<A NAME="RT16708SS-12B">12b</A> Kagiya T. Narisawa S. Maeda T. Fukui K. J. Polym. Sci., Part B: Polym. Lett. 1966, 4: 441

<A NAME="RT16708SS-12C">12c</A> Seeliger W. Aufderhaar E. Diepers W. Feinauer R. Nehring R. Thier W. Hellmann H. Angew. Chem., Int. Ed. Engl. 1966, 5: 875

<A NAME="RT16708SS-12D">12d</A> Bassiri TG. Levy A. Litt M. J. Polym. Sci., Part B: Polym. Lett. 1967, 5: 871

<A NAME="RT16708SS-13A">13a</A> Hoogenboom R. Fijten MWM. Thijs HML. Van Lankvelt BM. Schubert US. Designed Monomers Polym. 2005, 8: 659

<A NAME="RT16708SS-13B">13b</A> Beck M. Birnbrich P. Eicken U. Fischer H. Fristad WE. Hase B. Krause HJ. Angew. Makromol. Chem. 1994, 223: 217

<A NAME="RT16708SS-14A">14a</A> Adams N. Schubert US. Adv. Drug Delivery Rev. 2007, 59: 1504

<A NAME="RT16708SS-14B">14b</A> Aoi K. Okada M. Prog. Polym. Sci. 1996, 21: 151

<A NAME="RT16708SS-14C">14c</A> Kobayashi S. Uyama H. J. Polym. Sci., Part A: Polym. Chem. 2002, 40: 192

<A NAME="RT16708SS-15">15</A> Wiesbrock F. Hoogenboom R. Abeln CH. Schubert US. Macromol. Rapid Commun. 2004, 25: 1895

<A NAME="RT16708SS-16">16</A> Fijten MWM. Haensch C. Van Lankvelt BM. Hoogenboom R. Schubert US. Macromol. Chem. Phys. 2008, 209: 1887

<A NAME="RT16708SS-17A">17a</A> Wang J. Hanan GS. Synlett 2005, 1251

<A NAME="RT16708SS-17B">17b</A> Smith CB. Raston CL. Sobolev AN. Green Chem. 2005, 7: 650

<A NAME="RT16708SS-17C">17c</A> Winter A. van den Berg AMJ. Hoogenboom R. Kickelbick G. Schubert US. Synthesis 2006, 2873

<A NAME="RT16708SS-17D">17d</A> Winter A. Egbe DAM. Schubert US. Org. Lett. 2007, 9: 2345

<A NAME="RT16708SS-18">18</A> Tao C.-Z. Cui X. Li J. Liu A.-X. Liu L. Guo Q.-X. Tetrahedron Lett. 2007, 48: 3525

<A NAME="RT16708SS-19">19</A> This fragmentation in MALDI-TOF mass spectrometry is often observed for Ru(II)-bis(terpyridine) complexes, see, for example: Heller M. Schubert US. Macromol. Rapid Commun. 2002, 23: 411

<A NAME="RT16708SS-20">20</A> Vagin S. Frickenschmidt A. Kammerer B. Hanack M. Eur. J. Org. Chem. 2005, 3271

<A NAME="RT16708SS-21">21</A> Li Y. Huffman JC. Flood AH. Chem. Commun. 2007, 2692

A detailed investigation of the electrooptical properties of 1H-1,2,3-triazole-containing terpyridine derivatives, supported by DFT calculations is currently ongoing will be published elewhere.

<A NAME="RT16708SS-23">23</A> Winter A. Hummel J. Risch N. J. Org. Chem. 2006, 71: 4862