Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 48, Pages 13562-13573Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101934
Keywords
macrocycles; nitrogen heterocycles; nonlinear optics; porphyrinoids; tetrapyrroles
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Funding
- Science Foundation Ireland [09/IN.1/B2650]
- Science Foundation Ireland (SFI) [09/IN.1/B2650] Funding Source: Science Foundation Ireland (SFI)
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Current applications in porphyrin chemistry require the use of unsymmetrically substituted porphyrins. Many current industrial interests in optics and biomedicine require systems with either pushpull (electron-donating and -withdrawing groups) or amphiphilic systems (hydrophobic and hydrophilic groups). In this context we present the class of 5,10-A2B2-type porphyrins for which two different substituents are positioned in diagonally opposite meso positions. Thus, the intramolecular dipole moment in these tetrapyrroles is positioned along a beta-beta vector passing through two pyrrole rings. This is opposite to the situation of the frequently used 5,15-A2BC porphyrins for which the dipole moment is oriented along a mesomeso axis. We have elaborated syntheses of the 5,10-A2B2 porphyrins by using transition-metal-catalyzed transformations of 5,10-A2 porphyrins or direct substitutions reactions thereof; this gives the target molecules in 2277% overall yields. The compounds exhibit interesting structural, spectroscopic, and optical features and can serve as building blocks for new porphyrin arrays and applications.
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