Abstract
2-Mono- and 2,9-di-substituted 1,10-phenanthrolines with 4-pyridine units attached either via 1,4-phenylene- or 4-ethynyl-phenyl spacers, have been synthesised. The strategy is based on the introduction of 4-trimethylsilylphenyl group(s) at the phenanthroline core with the subsequent ipso-substitution of TMS groups by bromine or iodine and successive Suzuki or Sonogashira reactions with 4-pyridineboronic acid or 4-ethynylpyridine, respectively.
References
1.
Brandt W.W.
,
Dwyer F. P.
, and
Gyarfas E. C.
, Chem. Rev. , 1954 , 54 , 959 .
2.
Sammes P.G.
, and
Yahioglu G.
, Chem. Soc. Rev. , 1994 , 23 , 327 .
3.
Armaroli N.
, Chem. Soc. Rev. , 2001 , 30 , 113 .
4.
Sigman D.S.
, Acc. Chem. Res. , 1986 , 19 , 180 .
5.
Sigman D.S.
,
Bruicc T. W.
,
Mazumder A.
, and
Sutton C. L.
, Acct. Chem. Res. , 1993 , 26 , 98 .
6.
Collin J.P.
,
Dictrich-Buchecker C.
,
Gavina P.
,
Jimenes-Molcro M. C.
, and
Sauvage J.-P.
, Acct. Chem. Res. , 2001 , 34 , 477
7.
Sauvage J.-P.
, Acct. Chem. Res. , 1990 , 23 , 319 .
8.
Ibukuro F.
,
Fujita M.
,
Yamaguchi K.
, and
Sauvage J.-P.
, J. Am. Chem. Soc. , 1999 , 121 , 11041 .
9.
Dictrich-Buchecker C.
, and
Sauvage J.-P.
, Angew. Chem., Int. Ed. Engl. , 1989 , 28 , 189 .
10.
Schmittel M.
, and
Ganz A.
, Chem. Commun. , 1997 , 999 .
11.
Kalsani V.
,
Ammon H.
,
Jäckel F.
,
Rabe J. P.
, and
Schmittel M.
, Chem. Eur. J. , 2004 , 10 , 5481 .
12.
Schmittel M.
,
Kalsani V.
,
Kishore R. S. K.
,
Cölfen H.
, and
Bats J. W.
, J. Am. Chem. Soc. , 2005 , 127 , 11544 .
13.
Lüning U.
, and
Müller M
, Chem. Ber. , 1990 , 123 , 643 .
14.
Schmittel M.
, and
Michel C.
Abstracts Wissenschaftsforum Chemie 2007 , GDCh, Ulm, 2007 p. 549.
15.
Dictrich-Buchecker C.
,
Colasson B.
,
Fujita M.
,
Hori A.
,
Geum N.
,
Sakamoto S.
,
Yamaguchi K.
, and
Sauvage J.-P.
, J. Am. Chem. Soc. , 2003 , 125 , 5717 .
16.
Kotha S.
,
Lahiri K.
, and
Kashinath D.
, Tetrahedron , 2002 , 58 , 9633 .
17.
Chinchilla R.
, and
Nájcra C.
, Chem. Rev. , 2007 , 107 , 874 .
18.
Kozikowski A.P.
, Heterocycles , 1981 , 16 , 267
19.
Lamba J.J. S.
, and
Tour J. M.
J. Am. Chem. Soc. , 1994 , 116 , 11723 .
20.
Dictrich-Buchecker C.O.
, and
Sauvage J.-P.
, Tetrahedron Lett. , 1983 , 24 , 5091 .
21.
Grosshenny V.
, and
Ziessel R.
, Tetrahedron Lett , 1992 , 33 , 8075 .