Alihodžić, Sulejman; Žinić, Mladen
(1999)
Lariat ethers with pendant phenanthridine units. Synthesis and complexation of Na- and K-picrate..
Croatica Chemica Acta, 72
(4).
pp. 803-817.
ISSN 0011-1643
Abstract
Lariat ethers 12 and 13 with appended phenanthridine fluorophoric units have been prepared as potential fluorescent chemosensor molecules for alkaline metal salts possessing aromatic anions. The starting 8-ethyloxycarbonylamino-6-methylphenanthridine (1) was converted via 2, 3, 6 and 7 to N-(2-tosylethyl)-derivatives 4 and 8 suitable for N-alkylations of diaza- and aza-18-crown-6. However, the alkylations failed, giving the 2-oxazolidinone derivative 5 formed by intramolecular cyclization of phenanthridine N-carbamate derivatives 4 and 8 in basic conditions. The phenanthridine derivative 10 having benzyl instead carbamate protection on 8-amino group successfully alkylated mono- and diaza-crown ethers, giving lariats 12 and 14. Subsequent removal of benzyl protection groups in acidic conditions gave lariats 13 and 15. Lariat 12 was found to form unique Na- and K-picrate complexes with the metal cation bound in the crown cavity and picrate anion intercalated between phenanthridine units.
Item Type: |
Article
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Uncontrolled Keywords: |
crown ethers; lariate ethers; phenanthridine; complexes; sodium picrate; binding-properties; cation binding; crown ethers; fluorescence; recognition |
Subjects: |
NATURAL SCIENCES > Chemistry |
Divisions: |
Division of Organic Chemistry and Biochemistry |
Projects: |
Project title | Project leader | Project code | Project type |
---|
Projektiranje i sinteza supramolekularnih sustava | Mladen Žinić | 00980703 | MZOS |
|
Depositing User: |
Mladen Žinić
|
Date Deposited: |
25 Nov 2013 09:17 |
Last Modified: |
28 Feb 2014 12:15 |
URI: |
http://fulir.irb.hr/id/eprint/1101 |
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1101
WOS:000084489600008