Strongly coupled porphyrin arrays featuring both pi-cofacial and linear-pi-conjugative interactions.

Journal Article (Journal Article)

A combination of metal-catalyzed cross-coupling and metal-templated cycloaddition reactions have been utilized to establish multiporphyrin compounds 5-(5'-[15',15' '-bis(10' ',20' '-di[4-(3-methoxy-3-methylbutoxy)phenyl]porphinato)zinc(II)]ethyne)-6-[(5' "-10' ",20' "-di[4-(3-methoxy-3-methylbutoxy)phenyl]porphinato)zinc(II)]indane (1) and 5,6-bis(5'-15',15' '-bis[(10',20'-di[4-(3-methoxy-3-methylbutoxy)phenyl]porphinato)zinc(II)]ethyne)indane (2). Compounds 1 and 2 feature a covalently bridged cofacial bis(porphinato)metal core; ethyne bridging moieties conjugate directly one and two respective peripheral (porphinato)zinc(II) substituents to the macrocyclic framework of their corresponding face-to-face porphyrin units. Optical spectroscopy and electrochemical studies demonstrate substantive electronic interactions between the porphyrin subunits of these compounds. Notably, structural and (1)H NMR analyses verify that 1 and 2 possess open conformations necessary for binding small molecules within their respective cofacial (porphinato)metal cores.

Full Text

Duke Authors

Cited Authors

  • Fletcher, JT; Therien, MJ

Published Date

  • January 2002

Published In

Volume / Issue

  • 41 / 2

Start / End Page

  • 331 - 341

PubMed ID

  • 11800622

Electronic International Standard Serial Number (EISSN)

  • 1520-510X

International Standard Serial Number (ISSN)

  • 0020-1669

Digital Object Identifier (DOI)

  • 10.1021/ic010871p


  • eng