Towards the borphyrin : head-to-tail macrocycles based on boronate esters
Inspired by the versatility of boronic acid condensation with catechols, we set out to construct boronate-ester based macrocycles by the head-to-tail assembly of precursor that contains both a catechol and a boronic acid on the same molecule. A series of expanded “borphyrin” macrocycles was prepared...
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| Language: | English |
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University of British Columbia
2015
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| Online Access: | http://hdl.handle.net/2429/53634 |
| Summary: | Inspired by the versatility of boronic acid condensation with catechols, we set out to construct boronate-ester based macrocycles by the head-to-tail assembly of precursor that contains both a catechol and a boronic acid on the same molecule. A series of expanded “borphyrin” macrocycles was prepared in the pursuit of increasing the solubility.
Further characterization of the new macrocycles by UV-Vis and IR spectroscopy confirmed that they have extended conjugation. However, incorporation of sterically hindered bulky groups might also disrupt the trigonal planar geometry around the boron centers and limit the extent of conjugation of the macrocycles. === Science, Faculty of === Chemistry, Department of === Graduate |
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