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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University of British Columbia
2015
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| Online Access: | http://hdl.handle.net/2429/53634 |
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ndltd-UBC-oai-circle.library.ubc.ca-2429-536342018-01-05T17:28:13Z Towards the borphyrin : head-to-tail macrocycles based on boronate esters Lichen, Ni 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 2015-05-29T15:59:52Z 2016-05-31T00:00:00Z 2015 2015-09 Text Thesis/Dissertation http://hdl.handle.net/2429/53634 eng Attribution-NonCommercial-NoDerivs 2.5 Canada http://creativecommons.org/licenses/by-nc-nd/2.5/ca/ University of British Columbia |
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NDLTD |
| language |
English |
| sources |
NDLTD |
| description |
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 |
| author |
Lichen, Ni |
| spellingShingle |
Lichen, Ni Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| author_facet |
Lichen, Ni |
| author_sort |
Lichen, Ni |
| title |
Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| title_short |
Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| title_full |
Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| title_fullStr |
Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| title_full_unstemmed |
Towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| title_sort |
towards the borphyrin : head-to-tail macrocycles based on boronate esters |
| publisher |
University of British Columbia |
| publishDate |
2015 |
| url |
http://hdl.handle.net/2429/53634 |
| work_keys_str_mv |
AT lichenni towardstheborphyrinheadtotailmacrocyclesbasedonboronateesters |
| _version_ |
1718584765884399616 |