Synthesis, Characterization and Properties of Expanded Pyriporphyrins: A New Family of Alkylidenyl Porphyrin Homologues Bearing meso-Exocyclic Double Bonds

Abeje Abebayehu; Ranjan Dutta; Chang-Hee Lee

doi:10.1002/chem.201602136

Synthesis, Characterization and Properties of Expanded Pyriporphyrins: A New Family of Alkylidenyl Porphyrin Homologues Bearing meso-Exocyclic Double Bonds

Chemistry. 2016 Sep 19;22(39):13850-13856. doi: 10.1002/chem.201602136. Epub 2016 Jul 14.

Authors

Abeje Abebayehu¹, Ranjan Dutta¹, Chang-Hee Lee²

Affiliations

¹ Department of Chemistry, Kangwon National University, Chuncheon, 200-701, Korea.
² Department of Chemistry, Kangwon National University, Chuncheon, 200-701, Korea. chhlee@kangwon.ac.kr.

PMID: 27416016
DOI: 10.1002/chem.201602136

Abstract

We present the synthesis and characterization of a new family of expanded meso-alkylidenyl (2,6-pyri)porphyrinoids bearing multiple exocyclic double bonds at the meso-positions. The synthesis was accomplished by using mixed pyrrole condensation. Similar to meso-alkylidenyl porphyrinoids, this study revealed that pyriporphyrinoids do not possess a porphyrin-like, global-aromatic character. The synthesized 2,6-pyripentaphyrin 1 displays selective ratiometric sensing of pyrophosphate anion in organic solvent.

Keywords: anions; carbaporphyrins; meso-alkylidene; pyriporphyrin; sensors.