Details

Autor(en) / Beteiligte

• Senge, Mathias O.
• Fazekas, Marijana
• Pintea, Monica
• Zawadzka, Monika
• Blau, Werner J.

Titel

5,15-A2B2- and 5,15-A2BC-Type Porphyrins with Donor and Acceptor Groups for Use in Nonlinear Optics and Photodynamic Therapy

Ist Teil von

• European Journal of Organic Chemistry, 2011, Vol.2011 (29), p.5797-5816

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2011

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Development of efficient new synthetic strategies leading to more diversified substitution patterns of porphyrin rings is of great importance as it expands the potential applicability of these compounds and provides a more accurate way of tailoring their properties for a specific application. Changes in the electronic and conformational structures induced by different substituents are manifested by unique properties which are of interest for many applications ranging from amphiphilic porphyrins for photodynamic therapy, push–pull systems for optical applications, chiral systems useful in catalysis, to donor–acceptor systems suitable for electron transfer studies. Different chemical strategies were demonstrated for access to unsymetrically substituted porphyrins with nonequivalent β or meso substituents. For the latter we have adopted the functionalization of preformed porphyrins in order to obtain a diverse range of porphyrin structures with 5,15‐A2B2 and 5,15‐A2BC meso substitution patterns suitable for applications in optical limiting and photodynamic therapy. The functionalization of A2‐type starting materials by organolithium and palladium‐catalyzed cross‐coupling reactions is an efficient means to enable the introduction of almost any desired meso substituent. We report the nonlinear absorptive properties of our A2B2 and A2BC porphyrins and show that there is strong correlation between structural features and the optical limiting efficiency. The nonlinear optical studies indicate that the 5,15‐A2B2 substitution pattern provides more promising candidates for use in optical limiting. The synthesis and characterization of a range of A2B2‐ and A2BC‐type porphyrins indicates that the former are better candidates as optical limiters in nonlinear optics.