Abstract
The sterically hindered salicylaldimine ligands N,N‘-(1,5-diaminonaphthalene)-3,5-but2-salicylaldimine (L1), N,N‘-(2,7-diaminofluaren)-3,5-but2-salicylaldimine (L2) and N,N‘-(1,8-diaminonaphthaline)-3,5-but2-salicylaldimine (L3) have been synthesised by the condensation of 1,5-diaminonaphthalene, 2,7-diaminofluarene, and 1,8-diaminonaphthaline with 3,5-di-tert-butylsalicylaldehyde, respectively. Dinuclear M(II) complexes of L1 and L2 and mononuclear M(II) complexes of L3 have been prepared using Cu(II), Ni(II), Co(II), and Mn(II) salts and characterised. The synthesised sterically-hindered, salen-type complexes were tested as catalysts for the formation of cyclic carbonates from CO2 and liquid epoxides (propylene oxide, epichlorohydrine, 1,2-epoxybutane and styrene oxide), which served as both reactant and solvent. Ligand structure and the type of metal centre have a marked influence on the catalytic activity. Mn(II) complexes showed the highest catalytic activity.
References
1.
Casellato U.
, and
Vigato P.A.
, Coord. Chem. Rev. , 1977 , 23 , 31 .
2.
Dey K.
,
Biswas A.K.
, and
Roy A.
, Ind. J. Chem. , 1981 , 20 , 848 .
3.
Sunatsuki Y.
,
Motoda Y.
, and
Matsumoto N.
, Coord. Chem. Rev. , 2002 , 226 , 199 .
4.
Kilinçarslan R.
,
Karabiyik H.
,
Ulusoy M.
,
Aygün M.
,
Çetinkaya B.
, and
Büyükgüngör O.
, J. Coord. Chem. , 2006 , 59 , 1649 .
5.
Mascharak P.K.
, Coord. Chem. Rev. , 2002 , 225 , 201 .
6.
Kessissoglou D.P.
, Coord. Chem. Rev. , 1999 , 185–186 , 837 .
7.
Pyrz J.W.
,
Roe A.L.
,
Stern L.J.
, and
Que L.
J. Am. Chem. Soc. , 1985 , 107 , 614 .
8.
Chakraborty J.
, and
Patel R.N.
, J. Ind. Chem. Soc. , 1996 , 73 , 191 .
9.
Kilic A.
,
Tas E.
,
Deveci B.
, and
Yilmaz I.
, Polyhedron , 2007 , 26 , 4009 .
10.
Tas E.
,
Kilic A.
,
Durgun M.
,
Yilmaz I.
,
Özdemir I.
, and
Gurbuz N.
, J. Organomet. Chem. , 2009 , 694 , 446 .
11.
Ulusoy M.
,
Karabiyik H.
,
Kilincarslan R.
,
Aygun M.
, and
Cetinkaya B.
, Struct Chem. , 2008 , 19 , 749 .
12.
Behr A.
, Catalysis in C1 chemistry , ed.
Keim W.
, Reidel , Dordrecht , 1983 .
13.
Cohen C.T.
,
Thomas C.M.
,
Peretti K.L.
,
Lobkovsky E.B.
, and
Coates G.W.
, Dalton Trans. , 2006 , 237 .
14.
Darensbourg D.J.
,
Ulusoy M.
,
Karronnirun O.
,
Poland R.R.
, and
Reibenspies J.H.
, Macromolecules , 2009 , 42 , 6992 .
15.
Aida T.
, and
Inoue S.
, J. Am. Chem. Soc. , 1983 , 105 , 1304 .
16.
Mang S.
,
Cooper A.I.
,
Colclough M.E.
,
Chauhan N.
, and
Holmes A.B.
, Macromolecules , 2000 , 33 , 303 .
17.
Miller J.A.
,
Gross B.A.
,
Zhuravel M.A.
,
Jin W.
, and
Nguyen S.T.
, Angew. Chem. Int. Ed. , 2005 , 44 , 3885 .
18.
Lu X.B.
,
Zhang Y.J.
,
Liang B.
,
Li X.
, and
Wang H.
, J. Mol. Catal. A: Chem. , 2004 , 210 , 31 .
19.
Ramin M.
,
Jutz F.
,
Grunwaldt J.D.
, and
Baiker A.
, J. Mol. Catal. A: Chem. , 2005 , 242 , 32 .
20.
Zhao T.
,
Han Y.
, and
Sun Y.
, Phys. Chem. Chem., Phys. , 1999 , 1 , 3047 .
21.
Kawanami H.
, and
Ikushima Y.
, Chem. Commun. , 2000 , 2089 .
22.
Shen Y.M.
,
Duah W.L.
, and
Shi M.
, Adv. Synth. Catal. , 2003 , 345 , 337 .
23.
Yamaguchi K.
,
Ebitani K.
,
Yoshida T.
,
Yoshida H.
, and
Kaneda K.
, J. Am. Chem. Soc. , 1999 , 121 , 4526 .
24.
Yasuda H.
,
He L.N.
, and
Sakakura T.
, J. Catal. , 2002 , 209 , 547 .
25.
Doskocil E.J.
,
Bordawekar S.V.
,
Kaye B.C.
, and
Davis R.J.
, J. Phys. Chem B. , 1999 , 103 , 6277 .
26.
Peng J.
, and
Deng Y.
, New J. Chem. , 2001 , 25 , 639 .
27.
Ji D.
,
Lu X.
, and
He R.
, Appl. Catal. A: Gen. , 2000 , 203 , 329 .
28.
Paddock R.L.
, and
Nguyen S.T.
, J. Am. Chem. Soc. , 2001 , 123 , 11498 .
29.
Srivastava R.
,
Srinivas D.
, and
Ratnasamy R.
, Catal. Lett. , 2003 , 89 , 81 .
30.
Temel H.
,
Ilhan S.
,
Kilic A.
, and
Tas E.
, J. Coord. Chem. , 2008 , 61 (9 ), 1443 .
31.
Kumar K.N.
, and
Ramesh R.
, Polyhedron , 2005 , 24 (14 ), 1885 .
32.
Nakamoto K.
, Infrared and Raman Spectra of Inorganic and Coordination Compounds , 5th Ed., Wiley-Interscience , New York , 1997 . pp. 484.
33.
Sacconi L.
, Coord. Chem. Rev. , 1966 , 1 (1 ), 126 .
34.
Chen Z.
,
Wu Y.
,
Gu D.
, and
Gan F.
, Dyes and Pigments , 2008 , 76 (3 ), 624 .
35.
Ilhan S.
,
Temel H.
, and
Kilic A.
, J. Coord. Chem. , 2008 , 61 (2 ), 277 .
36.
Fraser C.
, and
Bosnich B.
, Inorg. Chem. , 1994 , 33 (2 ), 338 .
37.
Taha A.
, Spectrochim. Acta , 2003 , 59A , 1373 .
38.
Adolfo J.H.
,
Filgueiras C.A.L.
,
Wardell J.L.
,
Herbst M.H.
,
Vugman N.V.
,
Santos P.S.
,
Lopes J.G.S.
, and
Howie R.A.
, Inorg. Chim. Acta , 2004 , 357 , 4240 .
39.
Dutta R.L.
, Inorganic chemistry Part II , 2nd edn, The New Book Stall , Calcutta , 1981 . pp. 386 .
40.
Wu Q.G.
,
Esteghamatian M.
,
Hu N.X.
,
Popovic Z.
,
Enright G.
,
Wang S.
,
Tao Y.
, and
D'Iorio M.
, Chem. Mater. , 2000 , 12 , 79 .
41.
Ulusoy M.
,
Cetinkaya E.
, and
Cetinkaya B.
, Appl. Organometal. Chem. , 2009 , 23 , 68 .
42.
Darensbourg D.J.
,
Mackiewicz R.M.
, and
Billodeaux D.R.
, Organometallics , 2005 , 24 , 144 .
43.
Hodgson D.J.
, Prog. Inorg. Chem. , 1975 , 19 , 173 .
44.
Larrow J.F.
,
Jacobsen E.N.
,
Gao Y.
,
Hong Y.
,
Nie X.
, and
Zepp C.M.
, J. Org. Chem. , 1994 , 59 , 1939 .
45.
Earnshaw A.
, Introduction to magnetochemistry , Academic Press , London , 1968 , pp. 4 –8 .