Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(7): 1141-1147
DOI: 10.1055/s-2005-861855
DOI: 10.1055/s-2005-861855
PAPER
© Georg Thieme Verlag Stuttgart · New York
Phthalocyanine Synthesis in Ionic Liquids: Preparation of Differently Substituted Phthalocyanines in Tetrabutylammonium Bromide
Further Information
Received
24 November 2004
Publication Date:
10 March 2005 (online)
Publication History
Publication Date:
10 March 2005 (online)
Abstract
A series of alkylthio, alkoxy, and phenoxy phthalonitriles have been prepared by nucleophilic substitution reactions on suitable phthalonitrile precursors in molten tetrabutylammonium bromide. This readily available and inexpensive ionic liquid can also be used as a medium for the cyclization of these dinitriles giving the corresponding substituted phthalocyanines.
Key words
phthalonitriles - phthalocyanines - ionic liquids - nucleophilic substitution reactions
-
1a
Phthalocyanines - Properties and Applications
Vol. 1-4:
Leznoff CC.Lever ABP. VCH; New York: 1989-1996. -
1b
McKeown NB. Phthalocyanine Materials: Synthesis, Structure and Function Cambridge University Press; Cambridge: 1998. - See for example:
-
2a
Perry JW.Mansour K.Lee I.-YS.Wu X.-L.Bedworth PV.Chen C.-T.Ng D.Marder SR.Miles P.Wada T.Tian M.Sasabe H. Science 1996, 273: 1533 -
2b
Bao Z.Lovinger AJ.Dodabalapur A. Adv. Mater. 1997, 9: 42 -
2c
Bao Z.Lovinger AJ.Brown J. J. Am. Chem. Soc. 1998, 120: 207 -
2d
de la Torre G.Vázquez P.Agulló-López F.Torres T. J. Mater. Chem. 1998, 8: 1671 -
2e
Crone B.Dodabalapur A.Lin Y.-Y.Filas RW.Bao Z.LaDuca A.Sarpeshkar R.Katz HE.Li W. Nature 2000, 403: 521 -
2f
Schön JH.Kloc C.Bao Z.Batlogg B. Adv. Mater. 2000, 12: 1539 -
2g
Dini D.Barthel M.Hanack M. Eur. J. Inorg. Chem. 2001, 3759 - See for example:
-
3a
Meunier B.Sorokin A. Acc. Chem. Res. 1997, 30: 470 -
3b
Ito N.Etoh T.Hagiwara H.Kato M. Synthesis 1997, 153 -
3c
Ravikanth M.Achim C.Tyhonas JS.Münck E.Lindsey JS. J. Porphyrins Phthalocyanines 1997, 1: 385 -
3d
Oyaizu K.Haryono A.Natori J.Tsuchida E. J. Chem. Soc., Faraday Trans. 1998, 94: 3737 -
3e
Bench BA.Brennessel WW.Lee H.-J.Gorun SM. Angew. Chem. Int. Ed. 2002, 41: 750 -
3f
Tao X.Ma W.Zhang T.Zhao J. Chem. Eur. J. 2002, 8: 1321 - 4
Ali H.van Lier JE. Chem. Rev. 1999, 99: 2379 - 5
Erk P.Hengelsberg H. In The Porphyrin Handbook Vol. 19:Kadish KM.Smith KM.Guilard R. Academic Press; San Diego: 2003. Chap. 119. - 6
Sharman WM.van Lier JE. In The Porphyrin Handbook Vol. 15:Kadish KM.Smith KM.Guilard R. Academic Press; San Diego: 2003. Chap. 97. -
7a
Maree MD.Nyokong T. J. Chem. Res., Synop. 2001, 68 -
7b
Tolbin AY.Ivanov AV.Tomilova LG.Zefirov NS. J. Porphyrins Phthalocyanines 2003, 7: 162 -
7c
Liu L.-C.Hu AT. J. Porphyrins Phthalocyanines 2003, 7: 565 -
8a
Wöhrle D.Schmidt V. J. Chem. Soc., Dalton Trans. 1988, 549 -
8b
Frick K.Ziener U.Hanack M. Eur. J. Inorg. Chem. 1999, 1309 -
8c
Walsh CJ.Mandal BK. Chem. Mater. 2000, 12: 287 -
9a
Welton T. Chem. Rev. 1999, 99: 2071 -
9b
Wasser-scheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
9c
Sheldon R. Chem. Commun. 2001, 2399 -
9d
Dupont J.de Souza RF.Suarez PAZ. Chem. Rev. 2002, 102: 3667 -
9e
Wasserscheid P.Welton T. Ionic Liquids in Synthesis Wiley-VCH; Weinheim: 2003. -
10a A room temperature phthalocyanine-based molten salt, however, has been reported:
Dickinson E.Williams ME.Hendrickson SM.Masui H.Murray RW. J. Am. Chem. Soc. 1999, 121: 613 -
10b Catalytic oxidation of thiols by cobalt(II) phthalocyanines in ionic liquid has also been reported recently:
Chauhan SMS.Kumar A.Srinivas KA. Chem. Commun. 2003, 2348 -
11a
Kim DW.Song CE.Chi DY. J. Org. Chem. 2003, 68: 4281 -
11b
Liu Z.Chen Z.-C.Zheng Q.-G. Synthesis 2004, 33 -
12a
Gürol I.Ahsen V.Bekaroglu Ö. J. Chem. Soc., Dalton Trans. 1994, 497 -
12b
Del Rey B.Keller U.Torres T.Rojo G.Agulló-López F.Nonell S.Martí C.Brasselet S.Ledoux I.Zyss J. J. Am. Chem. Soc. 1998, 120: 12808 - 13 In a study of conjugate addition of thiols to electron deficient alkenes in molten Bu4NBr, Ranu et al. have suggested that the bromide ions form hydrogen bondings with the thiols, leading to an increase in their nucleophilicity:
Ranu BC.Dey SS.Hajra A. Tetrahedron 2003, 59: 2417 - See for example:
-
14a
Siegl WO. J. Heterocycl. Chem. 1981, 18: 1613 -
14b
Wöhrle D.Eskes M.Shigehara K.Yamada A. Synthesis 1993, 194 -
14c
Eberhardt W.Hanack M. Synthesis 1997, 95 -
14d
Liu W.Lee C.-H.Chan H.-S.Mak TCW.Ng DKP. Eur. J. Inorg. Chem. 2004, 286 -
15a
Wöhrle D.Schnurpfeil G.Knothe G. Dyes Pigments 1992, 18: 91 -
15b
Gürek AG.Bekaroglu Ö. J. Chem. Soc., Dalton Trans. 1994, 1419 -
15c
Lee C.-H.Ng DKP. Tetrahedron Lett. 2002, 43: 4211 - 16
Choi MTM.Li PPS.Ng DKP. Tetrahedron 2000, 56: 3881 - The following compounds have been described previously. See:
-
17a
For 2a and 2e: Ref. 12b.
-
17b
For 2b and 3b: Ref. 12a.
-
17c
Torres Cebada T,Sastre Santos A, andDel Rey Alvarez B. inventors; Spanish Patent ES 2116867. For 2c and 3c: ; Chem. Abstr. 1999, 130, 261059 -
17d
Taniguchi M,Narizuka T, andTomita H. inventors; Jpn. Kokai Tokkyo Koho JP 08269004. For 2d: ; Chem. Abstr. 1997, 126, 46981 -
17e
Duggan PJ, andGordon PF. inventors; Eur. Pat. Appl. EP 155780. For 2f: ; Chem. Abstr. 1986, 105, 70242 -
17f
Yamada A,Shigehara J,Kurata R, andHikosaka M. inventors; Jpn. Kokai Tokkyo Koho JP 61207365. For 2g: ; Chem. Abstr. 1987, 106, 32617 -
17g
For 2i: Ref. 14b.
-
17h For 2j:
Cook MJ.Dunn AJ.Howe SD.Thomson AJ.Harrison KJ. J. Chem. Soc., Perkin Trans. 1 1988, 2453 -
17i For 3a:
Suda Y.Shigehara K.Yamada A.Matsuda H.Okada S.Masaki A.Nakanishi H. Proc. SPIE-Int. Soc. Opt. Eng. 1991, 1560: 75 -
17j For 3d:
Shigehara K.Takizawa M.Takeda K. Synth. Met. 1995, 71: 2303 -
17k For 3e and 4d:
Eichhorn H.Wöhrle D.Pressner D. Liq. Cryst. 1997, 22: 643 -
17l
Ozawa H, andOshima K. inventors; Jpn. Kokai Tokkyo Koho JP 62139157. For 3f: ; Chem. Abstr. 1988, 108, 66063 -
17m
For 3g: Ref. 15c.
-
17n
For 4b: Ref. 16.
-
17o For 4c:
Ozoemena K.Westbroek P.Nyokong T. Electrochem. Commun. 2001, 3: 529 -
17p For 4e:
Nicolau M.del Rey B.Torres T.Mingotaud C.Delhaes P.Cook MJ.Thorpe SC. Synth. Met. 1999, 102: 1462