Structure and Spectroscopy of Free Base, Copper, and Zinc Tetrapentylporphyrin

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Abstract
Synthetic porphyrins have been crucial as models for heme units and other biological porphyrins, as well as components of advanced materials and catalysts. Much of the work on synthetic porphyrins has focused on the meso-substituted 5,10,15,20-tetraphenylporphyrin (TPP) or the pyrrole-substituted 2,3,7,8,12,13,17,18-octaethylporphyrin (OEP). In this report, we present a comprehensive spectroscopic, electrochemical, and computational study of free-base, zinc(II), and copper(II) 5,10,15,20-tetrapentylporphyrin (TPeP). TPeP can be prepared via a two-step, one-flask reaction of pyrrole and hexanal mediated by Montmorillonite K10, followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in yields of around 40%. Similar to TPP, the TPeP systems have the highest occupied molecular orbital (HOMO) with a2u symmetry and are, in general, easier to oxidize than their corresponding TPP or OEP analogues.
Funding Information
  • Division of Chemistry (CHE-2117141)
  • Division of Chemistry (CHE-2153091)
  • Colgate University
  • Division of Graduate Education (2152169)
  • University of Tennessee

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