Synthesis of an Unsymmetrically Substituted, Dithienylethene-Containing 1,10-Phenanthroline Ligand and its Ruthenium(II) Complex

Abstract

The synthesis of an unsymmetrically substituted 1,10-phenanthroline ligand and its corresponding ruthenium(II) complex is reported. Suzuki coupling has been employed under different conditions to get the target ligand.

metal complexes - cross-coupling - heterocycles - ligands - ruthenium

References

<A NAME="RZ03406SS-1A">1a</A> Tian H. Yang S. Chem. Soc. Rev.  2004,  33:  85 

<A NAME="RZ03406SS-1B">1b</A> Irie M. Chem. Rev.  2000,  100:  1685 

<A NAME="RZ03406SS-2A">2a</A> Adamo V. Belser P. Chimia  2003,  57:  169 

<A NAME="RZ03406SS-2B">2b</A> Chen B. Wang M. Wu Y. Tian H. Chem. Commun.  2002,  1060 

<A NAME="RZ03406SS-2C">2c</A> Fernandez-Acebes A. Lehn J.-M. Adv. Mater.  1998,  10:  1519 

<A NAME="RZ03406SS-2D">2d</A> Fernandez-Acebes A. Lehn J.-M. Chem. Eur. J.  1999,  5:  3285 

<A NAME="RZ03406SS-2E">2e</A> Fraysse S. Coudret C. Launay J.-P. Eur. J. Inorg. Chem.  2000,  1581 

<A NAME="RZ03406SS-2F">2f</A> Jukes RTF. Adamo V. Hartl F. Belser P. De Cola L. Inorg. Chem.  2004,  43:  2779 

<A NAME="RZ03406SS-2G">2g</A> Jukes RTF. Adamo V. Hartl F. Belser P. De Cola L. Coord. Chem. Rev.  2005,  249:  1327 

<A NAME="RZ03406SS-2H">2h</A> Konaka H. Wu LP. Munakata M. Kuroda-Sowa T. Maekawa M. Suenaga Y. Inorg. Chem.  2003,  42:  1928 

<A NAME="RZ03406SS-2I">2i</A> Matsuda K. Takayama K. Irie M. Inorg. Chem.  2004,  43:  482 

<A NAME="RZ03406SS-2J">2j</A> Matsuda K. Takayama K. Irie M. Chem. Commun.  2001,  363 

<A NAME="RZ03406SS-2K">2k</A> Munakata M. Wu LP. Kuroda-Sowa T. Bull. Chem. Soc. Jpn.  1997,  70:  1727 

<A NAME="RZ03406SS-2L">2l</A> Murguly E. Norsten TB. Branda NR. Angew. Chem. Int. Ed.  2001,  40:  1752 

<A NAME="RZ03406SS-2M">2m</A> Samachetty HD. Branda NR. Chem. Commun.  2005,  2840 

<A NAME="RZ03406SS-2N">2n</A> Sud D. McDonald R. Branda NR. Inorg. Chem.  2005,  44:  5960 

<A NAME="RZ03406SS-2O">2o</A> Takeshita M. Irie M. J. Org. Chem  1998,  63:  6643 

<A NAME="RZ03406SS-2P">2p</A> Takeshita M. Irie M. Tetrahedron Lett.  1998,  39:  613 

<A NAME="RZ03406SS-3">3</A> Belser P. De Cola L. Hartl F. Adamo V. Bozic B. Iyer YCVM. Jukes RTF. Kühni J. Querol M. Roma S. Salluce N. Adv. Funct. Mater.  2006,  16:  195 

<A NAME="RZ03406SS-4">4</A> Yam VW.-W. Ko C.-C. Zhu N. J. Am. Chem. Soc.  2004,  126:  12734 

<A NAME="RZ03406SS-5">5</A> Detty MR. Hays DS. Heterocycles  1995,  40:  925 

<A NAME="RZ03406SS-6A">6a</A> Irie M. Lifka T. Kobatake S. Kato N. J. Am. Chem. Soc.  2000,  122:  4871 

<A NAME="RZ03406SS-6B">6b</A> Kawai SH. Gilat SL. Ponsinet R. Lehn J.-M. Chem. Eur. J.  1995,  1:  285 

<A NAME="RZ03406SS-6C">6c</A> Lantz R. Hornfeldt AB. Chem. Scr.  1972,  2:  9 

<A NAME="RZ03406SS-7">7</A> Mlochowski J. J. Rocz. Chem.  1974,  48:  2145 

<A NAME="RZ03406SS-8">8</A>

¹H NMR (CDCl₃): δ = 9.34 (d, J = 4.1 Hz, 2 H), 8.29 (d, J = 8.3 Hz, 2 H), 7.71 (dd, J = 8.3, 4.3 Hz, 2 H), 7.46 (d, J = 6.0 Hz, 4 H), 7.30 (dd, J = 7.3, 6.1 Hz, 4 H), 7.25 (t, J = 7.1 Hz, 2 H), 2.75 (sept, J = 6.8 Hz, 2 H), 1.18 (d, J = 6.8 Hz, 3 H) 1.06 (d, J = 6.8 Hz, 3 H). MS (ESI+): m/z = 581.2 (M⁺ + 1).

<A NAME="RZ03406SS-9">9</A>

Kühni, J.; Adamo, V.; Belser, P. Chimia, submitted for publication.