Effect of meso aryl substituents on the synthesis of core-modified expanded porphyrins

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4847-4850

  Kumar, Rajeev ^b   Misra, Rajneesh ^b   Chandrashekar, Tavarekere K ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORPHYRINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33750352788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0619011     Document Type: Article

References (13)

1. (a) Sessler, J. L.; Weghorn, S. J. Expanded porphyrins. In The Porphyrin Handbook; Kadish, K. M, Ed.; Academic Press: San Diego, 2000; Vol. 2 and references cited therein.
2. (b) Chandrashekar, T. K.; Venkatraman, S. Acc. Chem. Res. 2003, 36, 677.
3. (c) Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In Expanded Porphyrins; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; San Diego, 2000.
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5. Narayanan, S. J.; Srinivasan, A.; Sridevi, B.; Chandrashekar, T. K.; Senge, M. O.; Sugiura, K.-I.; Sakata, Y. Eur. J. Org. Chem. 2000, 2357.
6. (a) Srinivasan, A.; Reddy, V. M.; Narayanan, S. J.; Sridevi, B.; Pushpan, S. K.; Kumar, M. R.; Chandrashekar, T. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2598.
7. (b) Srinivasan, A.; Pushpan, S. K.; Kumar, M. R.; Chandrashekar, T. K.; Roy, R. Tetrahedron 1999, 6671.
8. (c) Simi, K. P.; Venkataramana, G. A.; Sundararaman, V.; Alagar, S.; Akhilesh, K. G.; Chandrashekar, T. K. Tetrahedron Lett. 2001, 42, 3391.
9. Sessler, J. L.; Seidel, D.; Bucher, C.; Lynch, V. Chem. Commun. 2000, 1473.
10. A typical procedure for the condensation involves stirring of the mesityl-terthiophene diol (0.30g, 0.55 mmol) and 16 tripyrrane (0.27g, 0.55 mmol) in dry dichloromethane (200 mL) under a nitrogen atmosphere for 5 min at room temperature. Then, para-toluenesulphonic acid (0.03g, 0.165 mmol) was added to the above mixture. The solution was stirred for an additional 90 minutes. Chloranil (0.410 g, 1.65 mmol) was added, and the reaction mixture was exposed to air and refluxed for a further 90 min. The solvent was evaporated in a vacuum. The residue was purified by chromatography on a basic alumina column. The first red band which eluted with dichloromethane/petroleum ether (1:4) gave 10 in 22.2% yield (0.110 g).
11. Anand, V. G.; Pushpan, S. K.; Srinivasan, A.; Narayanan, S. J.; Sridevi, B.; Chandrashekar, T. K.; Roy, R.; Joshi, B. S. Org. Lett. 2000, 2, 3829.
12. Lash, T. D. Chem. - Eur. J. 1996, 2, 1197.
13. Sheldrick, G. M. SHELX-97; University of Göttingen: Göttingen, Germany, 1997.