Abstract
Nuclear magnetic resonance (NMR) spectroscopy and magnetic resonance imaging (MRI) have become important techniques in many research areas. One major limitation is the relatively low sensitivity of these methods, which recently has been addressed by hyperpolarization. However, once hyperpolarization is imparted on a molecule, the magnetization typically decays within relatively short times. Singlet states are well isolated from the environment, such that they acquire long lifetimes. We describe herein a model reaction for read-out of a hyperpolarized long-lived state in dimethyl maleate using thiol conjugate addition. This type of reaction could lend itself to monitoring oxidative stress or hypoxia by sensitive detection of thiols. Similar reactions could be used in biosensors or assays that exploit molecular switching. Singlet lifetimes of about 4.7 min for 1H spins in [D4]MeOH are seen in this system. Hyperpolarized singlet states are well isolated from the environment, such that they acquire long lifetimes. Here, we used the thiol conjugate addition to unveil the hyperpolarized long-lived singlet state in deuterated dimethyl maleate (see picture). Singlet lifetimes of 4.7 min for 1H spins in [D4]MeOH are seen in this system.
Original language | English (US) |
---|---|
Pages (from-to) | 3396-3399 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 53 |
Issue number | 13 |
DOIs | |
State | Published - Mar 24 2014 |
Keywords
- NMR spectroscopy
- cysteine
- long-lived spin states
- parahydrogen
- thiol conjugate addition
ASJC Scopus subject areas
- Catalysis
- General Chemistry