Functionalisation of Phthalocyanines and Subphthalocyanines by Transition-Metal-Catalysed Reactions

M. Victoria Martínez-Díaz; Maurizio Quintiliani; Tomás Torres

doi:10.1055/s-2007-1000823

ACCOUNT

Functionalisation of Phthalocyanines and Subphthalocyanines by Transition-Metal-Catalysed Reactions

M. Victoria Martínez-Díaz*, Maurizio Quintiliani, Tomás Torres*
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Fax: +34(91)4973966; e-Mail: tomas.torres@uam.es;

Abstract

Alle Artikel dieser Rubrik

Abstract

The functionalisation of phthalocyanines and subphthalocyanines by transition-metal-catalysed reactions is reviewed.

1 Introduction

2 Transition-metal-mediated cross-coupling reactions

2.1 Iodophthalocyanine and subphthalocyanine precursors

2.2 Alkynyl-substituted phthalocyanines and subphthalocyanines

2.3 Alkenyl-substituted phthalocyanines and subphthalocyanines

2.4 Aryl-substituted phthalocyanines and subphthalocyanines

2.5 Introduction of heteroatomic substituents in phthalocyanines and subphthalocyanines

3 Conclusions

Key words

phthalocyanines - subphthalocyanines - transition metals - cross-coupling reactions - palladium

Volltext

Referenzen

References

1a de la Torre G. Claessens CG. Torres T. Chem. Commun. 2007, 2000

1b Phthalocyanines: Properties and Applications Vols. 1-4: Leznoff CC. Lever ABP. VCH; Weinheim: 1989, 1993, 1996.

1c The Porphyrin Handbook Vols. 15-20: Kadish KM. Smith KM. Guilard R. Academic Press; San Diego: 2003.

1d McKeown NB. In Phthalocyanine Materials: Synthesis, Structure and Function Cambridge University Press; Cambridge UK: 1998.

2a de la Torre G. Torres T. Agulló-López F. Adv. Mater. 1997, 9: 265

2b de la Torre G. Vázquez P. Agulló-López F. Torres T. J. Mater. Chem. 1998, 8: 1671

2c de la Torre G. Vázquez P. Agulló-López F. Torres T. Chem. Rev. 2004, 104: 3723

2d Loi MA. Neugebauer H. Denk P. Brabec CJ. Sariciftci NS. Gouloumis A. Vázquez P. Torres T. J. Mater. Chem. 2003, 13: 700

2e Guldi DM. Gouloumis A. Vázquez P. Torres T. Georgakilas V. Prato M. J. Am. Chem. Soc. 2005, 127: 5811

3a Torres T. Gouloumis A. Sánchez-Garcia D. Jayawickramarajah J. Seitz W. Guldi DM. Sessler JL. Chem. Commun. 2007, 292

3b Ballesteros B. de la Torre G. Ehli C. Rahman GMA. Agulló-Rueda F. Guldi DM. Torres T. J. Am. Chem. Soc. 2007, 129: 5061

3c Morandeira A. López-Duarte I. Martínez-Díaz MV. O’Regan B. Shuttle C. Haji-Zainulabidin NA. Torres T. Palomares E. Durrant JR. J. Am. Chem. Soc. 2007, 129: 9250

4 de la Torre G. Claessens CG. Torres T. Eur. J. Org. Chem. 2000, 2821

5a Claessens CG. González-Rodríguez D. Torres T. Chem. Rev. 2002, 102: 835

5b Torres T. Angew. Chem. Int. Ed. 2006, 45: 961

5c Kobayashi N. In The Porphyrin Handbook Vol. 15: Kadish KM. Smith KM. Guilard R. Academic Press; San Diego: 2003. p.161

6a Sastre A. Torres T. Díaz-Garcia MA. Agulló-López F. Dhenaut C. Brasselet S. Ledoux I. Zyss J. J. Am. Chem. Soc. 1996, 118: 2746

6b del Rey B. Keller U. Torres T. Rojo G. Agulló-López F. Nonell S. Marti C. Brasselet S. Ledoux I. Zyss J. J. Am. Chem. Soc. 1998, 120: 12808

6c Claessens CG. González-Rodríguez D. Torres T. Martín G. Agulló-López F. Ledoux I. Zyss J. Ferro VR. García de la Vega JM. J. Phys. Chem. B 2005, 109: 3800

7a González-Rodríguez D. Torres T. Guldi DM. Rivera J. Herranz MA. Echegoyen L. J. Am. Chem. Soc. 2004, 126: 6301

7b González-Rodríguez D. Claessens CG. Torres T. Liu S. Echegoyen L. Vila S. Nonell N. Chem. Eur. J. 2005, 11: 3881

7c González-Rodríguez D. Torres T. Olmstead MM. Rivera J. Herranz MA. Echegoyen L. Atienza Castellanos C. Guldi DM. J. Am. Chem. Soc. 2006, 128: 10680

8 Sharman WM. van Lier JE. In The Porphyrin Handbook Vol. 15: Kadish KM. Smith KM. Guilards R. Academic Press; San Diego: 2003. p.1-59

9a de la Torre G. Torres T. J. Porphyrins Phthalocyanines 1997, 1: 221

9b Torres T. de la Torre G. Garcia-Ruiz J. Eur. J. Org. Chem. 1999, 2323

10 González-Cabello A. Vázquez P. Torres T. J. Organomet. Chem. 2001, 637-639: 751

11 González-Cabello A. Vázquez P. Torres T. Guldi DM. J. Org. Chem. 2003, 68: 8635

12 Sharman WM. van Lier JE. J. Porphyrins Phthalocyanines 2000, 4: 441

13 Ali H. van Lier JE. Tetrahedron Lett. 1997, 38: 1157

14 Maya EM. Vázquez P. Torres T. Chem. Commun. 1997, 1175

15 García-Frutos EM. Díaz DD. Vázquez P. Torres T. Synlett 2006, 3231

16 Tian M. Wada T. Kimura-Suda H. Sasabe H. J. Mater. Chem. 1997, 7: 861

17 Maya EM. García C. García-Frutos EM. Vázquez P. Torres T. J. Org. Chem. 2000, 65: 2733

18 García-Frutos EM. Fernández-Lázaro F. Maya EM. Vázquez P. Torres T. J. Org. Chem. 2000, 65: 6841

19 Ali H. St-Jean O. Tremblay-Morin J.-P. van Lier JE. Tetrahedron Lett. 2006, 47: 8275

20 Claessens CG. Torres T. Tetrahedron Lett. 2000, 41: 6361

21 Claessens CG. Torres T. Chem. Eur. J. 2000, 6: 2168

22 Bottari G. Díaz DD. Torres T. J. Porphyrins Phthalocyanines 2006, 10: 1083

23 Jiménez AJ. Spanig F. Rodríguez-Morgade MS. Ohkubo K. Fukuzumi S. Guldi DM. Torres T. Org. Lett. 2007, 9: 2481

24 García-Frutos EM. Bottari G. Vázquez P. Barberá J. Torres T. Chem. Commun. 2006, 3107

25 Claessens CG. Torres T. Chem. Commun. 2004, 1298

26 Jeffery T. Tetrahedron 1996, 52: 10113

27 Gouloumis A. Liu S.-G. Sastre A. Vázquez P. Echegoyen L. Torres T. Chem. Eur. J. 2000, 6: 3600

28 Gouloumis A. González-Rodríguez D. Vázquez P. Torres T. Liu S. Echegoyen L. Ramey J. Hug GL. Guldi DM. J. Am. Chem. Soc. 2006, 128: 12674

29 de la Escosura A. Martínez-Díaz MV. Guldi DM. Torres T. J. Am. Chem. Soc. 2006, 128: 4112

30 de la Escosura A. Martínez-Díaz MV. Thordarson P. Rowan AE. Nolte RJM. Torres T. J. Am. Chem. Soc. 2003, 125: 12300

31 Quintiliani M. García-Frutos EM. Gouloumis A. Vázquez P. Ledoux-Rak I. Zyss J. Claessens CG. Torres T. Eur. J. Org. Chem. 2005, 3911

32 Kimura M. Wada K. Ohta KM. Hanabusa K. Shirai H. Kobayashi N. Macromolecules 2001, 34: 4706

33a Kimura M. Ueki H. Ohta K. Hanabusa K. Shirai H. Kobayashi N. Langmuir 2002, 18: 7683

33b de la Escosura A. Martínez-Díaz MV. Torres T. Grubbs RH. Guldi DM. Neugebauer H. Winder C. Drees M. Sariciftci NS. Chem. Asian J. 2006, 1: 148

34a Aranyos V. Castaño AM. Grennberg H. Acta Chem. Scand. 1999, 53: 714

34b Kobayashi N. Fukuda T. Ueno K. Ogino H. J. Am. Chem. Soc. 2001, 123: 10740

34c Sugimori T. Okamoto S. Kotoh N. Handa M. Kasuga K. Chem. Lett. 2000, 1200

34d Sugimori T. Torikata M. Nojima J. Tominaka S. Tobikawa K. Handa M. Kasuga K. Inorg. Chem. Commun. 2002, 5: 1031

35 Espinet P. Echavarren A. Angew. Chem. Int. Ed. 2004, 43: 4704

36 Claessens CG. Torres T. J. Am. Chem. Soc. 2002, 124: 14522

37 Bottari G. Torres T. Chem. Commun. 2004, 2668

38 Achar BN. Lokesh KS. J. Organomet. Chem. 2004, 689: 3357

39 Wolfe JP. Buchwald SL. J. Org. Chem. 2000, 65: 1144

40 Tian H. Ali H. van Lier JE. Tetrahedron Lett. 2000, 8435

41 Soares ARM. Martínez-Díaz MV. Bruckner A. Pereira AMVM. Tome JPC. Alonso CMA. Faustino MAF. Neves MGPMS. Tome AC. Silva AMS. Cavaleiro JAS. Torres T. Guldi DM. Org. Lett. 2007, 9: 1557

42 Balch AL. Olmstead MM. Chem. Rev. 1998, 98: 2123

43 de la Torre G. Gouloumis A. Vázquez P. Torres T. Angew. Chem. Int. Ed. 2001, 40: 2895