Chromic and fluorescence response system based on the dihydrophenanthroline-bipyridine skeleton: dynamic redox behavior and metal binding properties

Tetrahedron Letters

Volumn 48, Issue 22, 2007, Pages 3823-3827

  Suzuki, Takanori ^a   Tamaki, Ryuuichi ^a   Ohta, Eisuke ^a   Takeda, Takashi ^a   Kawai, Hidetoshi ^a   Fujiwara, Kenshu ^a   Kato, Masako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Bipyridine; Dynamic redox system; Electrochromism; Fluorescence; Metal sensing

Indexed keywords

ACRIDINE DERIVATIVE; BIPYRIDINE; DIHYDROPHENANTHROLINE; PHENANTHROLINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; FLUORESCENCE; METAL BINDING; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

EID: 34247629532     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.167     Document Type: Article

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15. + units against intermolecular nucleophilic attack by pyridine lone pairs.
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19. 2+.
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21. i-symmetric in crystal, and non-bonded C⋯N distance is 2.62 Å and the dihedral angle between two benzene nuclei of the acridinium is 13.4°.
22. 2+ than the dihydrophenanthrene derivative (Ref. 4a) may be accounted for by donation of nitrogen lone pairs to the fluorophores.
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26. n+ and Lewis basicity of solvents may account for the observation.
27. 2. Similar stepwise process were also observed during oxidation of some dynamic redox systems, where two cationic parts are forced to locate in proximity (Refs. 4e,f).