Rational routes to formyl-substituted chlorins.
Two distinct approaches have been developed for the synthesis of chlorins bearing formyl groups: (1) reaction of an acetal-substituted 1-acyldipyrromethane with 2,3,5,6-tetrahydro-1,3,3-trimethyldipyrrin to give upon hydrolysis a 5-formylchlorin and (2) Pd-mediated coupling of a bromochlorin with a one-carbon synthon (hydroxymethyl tributyltin or CO) to give a 13-, 15-, or 3,13-formylchlorin. The zinc chlorins exhibit long-wavelength peak absorption maxima ranging from 626 to 667 nm, indicating the wavelength tunability afforded by formyl substitution.
Muthiah
Chinnasamy
C
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA. jlindsey@ncsu.edu
Bhaumik
Jayeeta
J
Lindsey
Jonathan S
JS
D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
D011166:Porphyrins; C006969:chlorin