The first electroresponsive phenylazomethine macrocycles: Highly preferential formation and regular molecular packing

Organic Letters

Volumn 5, Issue 3, 2003, Pages 345-347

  Higuchi, Masayoshi ^a   Kanazawa, Hirohiko ^a   Yamamoto, Kimihisa ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; MACROCYCLIC COMPOUND; MONOMER; TITANIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; POLYMERIZATION;

EID: 0038335649     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0273755     Document Type: Article

References (19)

1. (a) Higuchi, M.; Shiki, S.; Yamamoto, K. Org. Lett. 2000, 2, 3079.
2. (b) Higuchi, M.; Shiki, S.; Ariga, K.; Yamamoto, K. J. Am. Chem. Soc. 2001, 123, 4414.
3. (c) Yamamoto, K.; Higuchi, M.; Shiki, S.; Tsuruta, M.; Chiba, H. Nature 2002, 415, 509.
4. (a) Morgan, P. W.; Kwolek, S. L.; Pletcher, T. C. Macromolecules 1987, 20, 729.
5. (b) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1991, 3, 878.
6. (c) Park, S. B.; Kim, H.; Zin, W. C.; Jung, J. C. Macromolecules 1993, 26, 1627.
7. (d) Yang, C. J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180.
8. (e) Thomas, O.; Inganäs, O.; Andersson, M. R. Macromolecules 1998, 31, 2676.
9. (a) Higuchi, M.; Yamamoto, K. Org. Lett. 1999, 1, 1881.
10. (b) Higuchi, M.; Kimoto, A.; Shiki, S.; Yamamoto, K. J. Org. Chem. 2000, 65, 5680.
11. (c) Higuchi, M.; Kanazawa, H.; Tsuruta, M.; Yamamoto, K. Macromolecules 2001, 34, 8847.
12. Further addition of the diamine monomer is needed in the AABB-type polycondensation in order to compensate for the amount of diamine monomer consumed in the neutralization of HCl, which is generated in the dehydration. Of course, the polycondensation is carried out in a large excess of DABCO, which prevents the neutralization of HCl with the diamine monomer. However, the neutralization of HCl with the diamine monomer is not prevented completely, even in the presence of a large excess of DABCO. In fact, linear oligomers having carbonyl groups at both ends remain in the reaction mixture before further addition of the diamine monomer, which was confirmed by TOF-MS measurement. Total cyclization of the linear oligomers is extremely important for easy isolation of the cyclic oligomers, which is achieved by the further addition of the diamine monomer.
13. 6-aabb were obtained because crystal packing forces the equilibrium to shift toward one isomer.
14. For stacking and crystal structures of conjugated macrocycles, see the following: (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350. (d) Nitschke, J. R.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345. (e) Tain, Y.; Tong, J.; Frenzen, G.; Sun, J. J. Org. Chem. 1999, 64, 1442.
15. For stacking and crystal structures of conjugated macrocycles, see the following: (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350. (d) Nitschke, J. R.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345. (e) Tain, Y.; Tong, J.; Frenzen, G.; Sun, J. J. Org. Chem. 1999, 64, 1442.
16. For stacking and crystal structures of conjugated macrocycles, see the following: (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350. (d) Nitschke, J. R.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345. (e) Tain, Y.; Tong, J.; Frenzen, G.; Sun, J. J. Org. Chem. 1999, 64, 1442.
17. For stacking and crystal structures of conjugated macrocycles, see the following: (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350. (d) Nitschke, J. R.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345. (e) Tain, Y.; Tong, J.; Frenzen, G.; Sun, J. J. Org. Chem. 1999, 64, 1442.
18. For stacking and crystal structures of conjugated macrocycles, see the following: (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350. (d) Nitschke, J. R.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345. (e) Tain, Y.; Tong, J.; Frenzen, G.; Sun, J. J. Org. Chem. 1999, 64, 1442.
19. The -CH=N- bonds in conventional PPAs are unstable during the electrochemical measurements in the acidic solution, but the -CPh=Nbonds in CPAn are rather stable, because a phenyl group at the α-position of the imine bond stabilizes both the radical species (Rad) and the quinoidal one (Qn) formed during the measurements.