Lariat ethers with pendant phenanthridine units. Synthesis and complexation of Na- and K-picrate.

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

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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

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: