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A Heck-type coupling for the synthesis of novel bridged metallochlorin-fullerene C-60 dyads

M. Katterle ; A. R. Holzwarth ; Aldo Jesorka (Institutionen för kemi- och bioteknik, Fysikalisk kemi)
European Journal of Organic Chemistry (1434-193X). 2, p. 414-422. (2006)
[Artikel, refereegranskad vetenskaplig]

A short and convenient synthesis of metallochlorin-C-60 dyads based on a Heck-type hetero coupling at the 3(2) position of a chlorin is described. p-Bromobenzaldehyde was treated with Zn-metalated 13(2)-demethoxycarbonylmethylpheophorbide a, using a palladium acetate/LiCl catalyst mixture under phase-transfer conditions in DMF at 70 degrees C. The resulting asymmetric olefin was obtained in a high trans/cis ratio. The desired trans isomer was separated and subsequently transformed into a donor-acceptor dyad by a 1,3-dipolar cycloaddition to C-60 in the presence of sarcosine in refluxing toluene. The resulting dyads are expected to undergo efficient photoinduced electron transfer and can potentially be utilized in solar energy conversion devices. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

Denna post skapades 2007-02-05. Senast ändrad 2007-08-27.
CPL Pubid: 26232


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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Fysikalisk kemi (2005-2014)



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