Dipyrrin-Bis(N-Confused Porphyrin) Conjugate: Synthesis, Synergetic Ligation and Chirality Sensing

Jacek Wojaczyński; Justyna Maciołek; Piotr J Chmielewski

doi:10.1002/asia.201700129

Dipyrrin-Bis(N-Confused Porphyrin) Conjugate: Synthesis, Synergetic Ligation and Chirality Sensing

Chem Asian J. 2017 Mar 16;12(6):643-647. doi: 10.1002/asia.201700129. Epub 2017 Feb 16.

Authors

Jacek Wojaczyński¹, Justyna Maciołek¹, Piotr J Chmielewski¹

Affiliation

¹ Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50383, Wrocław, Poland.

PMID: 28134498
DOI: 10.1002/asia.201700129

Abstract

A fully conjugated system 4 consisting of two 2-aza-21-carbaporphyrin (NCP) subunits bridged by dipyrrin was synthesized by a highly selective condensation of 3-pyrrole-NCP 2 with aryl aldehydes. The free base 4 as well as its silver(III) complex 5 exhibited flexibility of the bridge allowing synergetic binding of Ag^I , thus leading to a mixed-valence tetraporphyrinic assembly consisting of eight silver atoms which was characterized both in the solid state and in solution. Binding of chiral acid by 4 and 5 was shown by observation of an induced optical activity of the adducts.

Keywords: dimerization; dipyrrin; porphyrinoids; self-assembly; silver complexes.