One-step synthesis and characterization of difunctionalized N-confused tetraphenylporphyrins

The Journal of Organic Chemistry
Shana A WolffDavid A Modarelli

Abstract

Three disubstituted N-confused porphyrins (2-4) were prepared in ca. 4% yield using a one-pot synthesis. These porphyrins bear 3,5-di-tert-butylphenyl groups substituted at the C(5) and C(20) meso positions and para-substituted (Br, NO(2), ethynyl) phenyl groups at the C(10) and C(15) meso positions. The specific orientation of the aryl rings around the macrocycle in porphyrin 2 was definitively determined using a combination of 1D ((1)H and (13)C) and 2D (gHMQC and gHMBC) NMR spectroscopy. The absorption spectra of 2-4 in CH(2)Cl(2) and dimethylacetamide are similar to those of N-confused tetraphenylporphyrin in the same solvents but have Soret and Q-bands that are shifted to lower energies. Steady-state fluorescence measurements revealed Q(x)(0,0) and Q(x)(0,1) bands similar in energy to the unsubstituted NCPs 1i and 1e. The fluorescence quantum yield results for two of these NCPs (2, 4) are atypical of porphyrin behavior and are being further investigated by time-resolved spectroscopy.

References

May 31, 1972·Journal of the American Chemical Society·M S PoonianA L Nussbaum
May 29, 2000·Organic Letters·G R GeierJ S Lindsey
May 25, 2002·The Journal of Organic Chemistry·Arounaguiry AmbroiseJonathan S Lindsey
Jul 18, 2002·Journal of the American Chemical Society·Kimihiro Susumu, Michael J Therien
Dec 3, 2002·Nature·Ira M BennettDevens Gust
Jul 17, 2003·Journal of the American Chemical Society·Naomi P RedmoreMichael J Therien
Jul 17, 2003·Angewandte Chemie·Mikael AnderssonMichael R Wasielewski

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Citations

Sep 9, 2011·Chemical Communications : Chem Comm·Motoki Toganoh, Hiroyuki Furuta
Sep 24, 2015·Chemistry : a European Journal·Lina YeKarl M Kadish
Jul 14, 2006·The Journal of Physical Chemistry. a·Elvin A AlemánDavid A Modarelli
Jun 27, 2012·The Journal of Organic Chemistry·Rajendra AcharyaDavid A Modarelli
Oct 23, 2004·The Journal of Organic Chemistry·Janet L ShawDavid A Modarelli

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