Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor
- Authors
- Lee, Min Hee; Yoon, Byungkwon; Kim, Jong Seung; Sessler, Jonathan L.
- Issue Date
- 2013
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- CHEMICAL SCIENCE, v.4, no.11, pp.4121 - 4126
- Indexed
- SCIE
SCOPUS
- Journal Title
- CHEMICAL SCIENCE
- Volume
- 4
- Number
- 11
- Start Page
- 4121
- End Page
- 4126
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/106592
- DOI
- 10.1039/c3sc51813b
- ISSN
- 2041-6520
- Abstract
- The trifluoroacetyl acetonate naphthalimide derivative 1 has been synthesized in good yield. In acetonitrile solution, compound 1 reacts selectively with hydrazine (NH2NH2) to give a five-membered ring. This leads to OFF-ON fluorescence with a maximum intensity at 501 nm as well as easily discernible color changes. Based on a readily discernible and reproducible 3.9% change in overall fluorescence intensity, the limit of detection for 1 is 3.2 ppb (0.1 mu M), which is below the accepted limit for hydrazine set by the U.S. Environmental Protection Agency (EPA). Compound 1 is selective for hydrazine over other amines, including NH4OH, NH2OH, ethylenediamine, methylamine, n-butylamine, piperazine, dimethylamine, triethylamine, pyridine, and is not perturbed by environmentally abundant metal ions. When supported on glass-backed silica gel TLC plates, compound 1 acts as a fluorimetric and colorimetric probe for hydrazine vapor at a partial pressure of 9.0 mm Hg, with selectivity over other potentially interfering volatile analytes, including ammonia, methylamine, n-butylamine, formaldehyde, acetaldehyde, H2O2, HCl, and CO2 being observed. Probe 1 can also be used for the detection of hydrazine in HeLa cells and does so without appreciable interference from other biologically abundant amines and metal ions.
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