PMID: 11925216Apr 2, 2002Paper

Glaser-mediated synthesis and photophysical characterization of diphenylbutadiyne-linked porphyrin dyads

The Journal of Organic Chemistry
W Justin YoungbloodJ S Lindsey

Abstract

The Pd-mediated Glaser coupling of a zinc monoethynyl porphyrin and a magnesium monoethynyl porphyrin affords a mixture of three 4,4'-diphenylbutadiyne-linked dyads comprised of two zinc porphyrins (Zn-pbp-Zn), two magnesium porphyrins (Mg-pbp-Mg), and one metalloporphyrin of each type (Zn-pbp-Mg). The latter is easily isolated due to the greater polarity of the magnesium versus the zinc chelate. Exposure of Zn-pbp-Mg to silica gel results in selective demetalation, affording Zn-pbp-Fb where Fb = free base porphyrin. This synthesis route employs the magnesium porphyrin as a latent form of the Fb porphyrin, thereby avoiding copper insertion during the Glaser reaction, and as a polar entity facilitating separation. The absorption spectrum of Zn-pbp-Mg or Zn-pbp-Fb is the sum of the spectra of the component parts, while in each case the fluorescence spectrum upon illumination of the Zn porphyrin is dominated by emission from the Mg or Fb porphyrin. Time-resolved absorption spectroscopy shows that the energy-transfer rate constants are (11 ps)(-1) and (37 ps)(-1) for Zn-pbp-Mg and Zn-pbp-Fb, respectively, corresponding to energy-transfer quantum yields of 0.995 and 0.983, respectively. The calculated Förster through-space rates are...Continue Reading

Citations

Oct 7, 2016·Chemical Reviews·Satoru HirotoHiroshi Shinokubo
Dec 28, 2016·The Journal of Organic Chemistry·Sudhakar Gaikwad, Michael Schmittel
Jul 4, 2017·Chemical Communications : Chem Comm·Sudhakar GaikwadMichael Schmittel
Jul 28, 2015·Organic & Biomolecular Chemistry·Michael SchmittelSusnata Pramanik
Feb 28, 2013·Chemistry, an Asian Journal·Adina I CiuciuDaniel T Gryko
Aug 3, 2018·Drug Development Research·Michael R Hamblin, Heidi Abrahamse
Jul 30, 2011·Physical Chemistry Chemical Physics : PCCP·Peter W ThulstrupJens Spanget-Larsen
Dec 8, 2009·The Journal of Physical Chemistry. B·Hee-Eun SongDewey Holten
Feb 5, 2009·The Journal of Physical Chemistry. B·Martin RegehlyBeate Röder
Jun 21, 2007·The Journal of Organic Chemistry·Patchanita ThamyongkitJonathan S Lindsey
Nov 11, 2003·Inorganic Chemistry·Karl-Heinz SchweikartJonathan S Lindsey
Aug 24, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·Marta KopaczyñskaJurgen-Hinrich Fuhrhop
Dec 27, 2005·The Journal of Physical Chemistry. B·Lingyun WeiDavid F Bocian
Oct 14, 2003·Inorganic Chemistry·Igor V SazanovichDewey Holten

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