Synthesis and Characterization of Thiol-Derivatized Porphyrins and Metalloporphyrin complexes

✍ Scribed by Hongping Yuan; L. Keith Woo

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 241 KB
• Volume: 01
• Category: Article
• ISSN: 1088-4246
• DOI: 10.1002/(sici)1099-1409(199704)1:2<189::aid-jpp23>3.0.co;2-g

✦ Synopsis

A series of thiol-derivatized porphyrins and the corresponding cobalt and zinc complexes were synthesized from 5-(p-aminophenyl)-10,15,20-triphenylporphyrin (H 2 TPP-NH 2 ), and 5α,15α-bis(o-aminophenyl)porphyrin (H 2 DPE-(NH 2 ) 2 ). These derivatized porphyrins have a different number of thiol appendages attached via amide linkages at different locations. The thiol-derivatized porphyrins made from H 2 TPP-NH 2 , H 2 TPP-NHC(O)(CH 2 ) n SH (n = 2, 4, 5, 10), have one alkyl-thiol appendage attached to the porphyrin through an amide linkage on the p-aminophenyl position. The derivatives made from H 2 DPE-(NH 2 ) 2 have two alkyl-thiol appendages attached to the porphyrin through amide linkages on the o-aminophenyl positions on the same face of the porphyrin ring. These thiol-derivatized porphyrins are important adsorbates for the preparation of thiol-porphyrin monolayers on gold.