Synthesis and electronic properties of trimeric octaethylporphyrin (OEP) derivative connected with diacetylene linkage. A comparative study with vinylene-group connected OEP trimer

Science and Technology of Advanced Materials

Volumn 7, Issue 3, 2006, Pages 237-242

  Hayashi, Naoto ^a   Sato, Misuzu ^a   Miyabayashi, Keiko ^b   Miyake, Mikio ^b   Higuchi, Hiroyuki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Diacetylene; Electronic property; Porphyrin; Trimer; Vilsmeier formylation; Vinylene

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; ELECTRONIC PROPERTIES; POLYACETYLENES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DIACETYLENE; TRIMERS; VILSMEIER FORMYLATION; VINYLENE;

DERIVATIVES;

EID: 33747308406     PISSN: 14686996     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.stam.2005.12.006     Document Type: Article

References (24)

1. Only a few recent articles of the π-electronic extended systems of porphyrin nuclei with various linkages are shown. Lukas A.S., Bushard P.J., and Wasielewski M.R. Electron transfer involving nonbonded superexchange interactions in rigid donor-acceptor arrays. J. Phys. Chem. A 106 (2002) 2074-2082
2. ElKhouly M.E., Arai Y., Fujitsuka M., and Ito O. Photoinduced electron transfer between metal octaethylporphyrins and fullerenes (C60/C70) studied by laser ash photolysis: electron-mediating and hole-shifting cycles. Phys. Chem. Chem. Phys. 4 (2002) 3322-3329
3. Zenkevich E.I., Borczykowski C., and Shul'ga A.M. Structure and excited state properties of multiporphyrin arrays formed by supramolecular design. J. Porphyrins Phthalocyanines 7 (2003) 731-754
4. Schuster D.I., Cheng P., Jarowski P.D., Guldi D.M., Luo C.P., Echegoyen L., Pyo S., Holzwarth A.R., Braslavsky S.E., Williams R.M., and Klihm G. Design, synthesis, and photophysical studies of a porphyrin-fullerene dyad with parachute topology; charge recombination in the Marcus inverted region. J. Am. Chem. Soc. 126 (2004) 7257-7270
5. Hayashi N., Murayama M., Mori K., Matsuda A., Chikamatsu E., Tani K., Miyabayashi K., Miyake M., and Higuchi H. Syntheses and electronic properties of the nickel and palladium complexes of the octaethylporphyrin(M1)-(dihexylbithiophene)n-octaethylporphyrin(M2) system [OEP(M1)-(DHBTh)n-OEP(M2)] connected with the diacetylene linkage. A methodology for molecular design of the particular electronic structure. Tetrahedron 60 (2004) 6363-6383
6. A part of this work was preliminarily reported. Hayashi N., Sato M., Miyabayashi K., Miyake M., and Higuchi H. Synthesis and electronic properties of trinucleic porphyrin derivative connected with diacetylene linkage. JAIST Int. Symp. Nano Technol., Symp. Proc. (2005) 94-95
7. Eglinton G., and Galbraith A.R. Cyclic diynes. Chem. Ind. (1956) 737-738
8. Anderson H.L. Meso-alkynyl porphyrins. Tetrahedron Lett. 33 (1992) 1101-1104
9. Arnold D.P., Johnson A.W., and Mahendran M. Some reactions of meso-formyloctaethylporphyrin. J. Chem. Soc., Perkin Trans. 1 (1978) 366-370
10. Ponomarev G.V., and Shul'ga A.M. First synthesis of ethylenebisporphyrins. Khim. Geterotskil. Soedin. (1986) 278-279
11. Higuchi H., Shimizu K., Ojima J., Sugiura K., and Sakata Y. Synthesis and properties of etheno-bridged porphyrin trimers. Tetrahedron Lett. 36 (1995) 5359-5362
12. Higuchi H., Takeuchi M., and Ojima J. Mono-, di-, and trimetallic palladium(II) porphyrin trimers with etheno-bridge. Chem. Lett. (1996) 593-594
13. Higuchi H., Shimizu K., Takeuchi M., Ojima J., Sugiura K., and Sakata Y. Synthesis and properties of tris(octaethylporphyrin)s connected with vinylene groups. Bull. Chem. Soc. Jpn 70 (1997) 1923-1933
14. 8 transition-metal complexes of vinylene-bridged bis- and tris(octaethylporphyrin)s. Bull. Chem. Soc. Jpn 72 (1999) 1887-1898
15. Higuchi H., Takeuchi M., Hashegawa Y., and Ojima J. Synthesis and electronic properties of Ni-Pd-Pt complex of vinylene-bridged tris(octaethylporphyrin). Non-linear Opt. 22 (1999) 333-336
16. Higuchi H., Shinbo M., Usuki M., Takeuchi M., Tani K., and Yamamoto K. Synthesis and structural and electronic properties of the mixed complexes of vinylene-bridged bis- and tris(octaethylporphyrin)s with Ni(II) Pd(II), and Pt(II) ions. Bull. Chem. Soc. Jpn 73 (2000) 1259-1275
17. Vilsmeier A., and Haack A. Uber die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Ein neue Methode zur Darstellung sekundärer und tertiärer p-Alkylamino-benzaldehyde. Ber. 60 (1927) 119-122
18. Campaigne E., and Archer W.L. p-Dimethylaminobenzaldehyde. Org. Synth. Coll. 4 (1963) 331-333
19. Inhoffen H.H., Fuhrhop J.H., Voigt H., and Brockmann Jr. H. Formylierung der meso-Kohlenstoffatome von Alkyl-substituierten Porphyrinen. Justus Liebigs Ann. Chem. 695 (1966) 133-143
20. Vicente M.G.H., and Smith K.M. Vilsmeier reactions of porphyrins and chlorins with 3-(dimethylamino)acrolein to give meso-(2-formylvinyl)porphyrins: new syntheses of benzochlorins, benzoisobacteriochlorins, and benzobacteriochlorins and reductive coupling of porphyrins and chlorins using low-valent titanium complexes. J. Org. Chem. 56 (1991) 4407-4418
21. -2 mmol of the starting materials and 15-20 eq. amount of the Vilsmeier reagent, under the limited conditions of which the monoformylation product from 3 was obtained in 70-75% yield. Also see Experimental part as general procedure for Vilsmeier formylation of 3.
22. 3).
23. 3).
24. Studies on the quantitative analysis of the spectral change of 1 in pyridine and on the theoretical interpretation of the position-selectivity in Vilsmeier monoformylation are now underway. The results will be reported in detail properly, together with an application of the present result to the construction of the π-electronic conjugation systems of the new type such as two-dimensional diacetylene- and vinylene-groups connected OEP oligomers.