Journal
DYES AND PIGMENTS
Volume 194, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2021.109618
Keywords
Infrared absorption; Isotope effect; Mass spectrometry; Proton nuclear magnetic resonance; Substitution effect; Visible absorption
Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [JP17H06436, I4LEC]
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The 3-vinyl group of methyl pyropheophorbide-a was chemically transformed into partially or fully deuterated groups through various reactions. Regioselectively deuterated pyropheophorbides were obtained with minimal loss of deuteration degree compared to the starting materials. Deuteration largely affected the infrared vibrational bands, slightly impacted specific proton signals, and did not change visible absorption bands in a solution.
The 3-vinyl group of methyl pyropheophorbide-a, one of the chlorophyll-a derivatives, was chemically transformed into partially or fully deuterated vinyl, 1-hydroxyethyl, acetyl, formyl, and hydroxymethyl groups via oxidation, oxidative cleavage, reduction, dehydration, or Grignard reaction. Using commercially available sodium borodeuteride and trideuteromethyl iodide as deuterium sources, a variety of regioselectively deuterated pyropheophorbides were obtained with either no or a slight loss of the deuteration degree compared with those of the starting deuterated materials. The deuteration affected largely the related infrared vibrational bands, slightly the chemical shifts of specific proton signals, and no change of visible absorption bands in a solution.
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