Second generation calixpyrrole anion sensors [28]

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9350-9351

  Anzenbacher Jr , Pavel ^a   Jursíková, Karolina ^a   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ANION; CALIXPYRROLE; CHLORIDE ION; FLUORIDE; PHOSPHATE; PYROPHOSPHATE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; FLUORESCENCE; HYDROGEN BOND; LETTER; LIGAND BINDING; SENSOR; SOLUBILITY; STOICHIOMETRY; SYNTHESIS;

EID: 0343443051     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001308t     Document Type: Letter

References (20)

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15. Sensor 1 (fluorescent label: dansyl) has absorption maximum λ = 350 nm, emission λ = 520 nm, Φ = 0.36; sensor 2 (fluorescent label: Lissamine) has absorption maximum λ = 550 nm, emission λ = 575 nm, Φ = 0.18; sensor 3 (fluorescent label: fluorescein) has absorption maximum λ = 510 nm, emission λ = 525 nm, Φ = 0.42. Fluorescence quantum yields (Φ) were measured following the method described by Demas and Crosby (Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991-1024) with quinine sulfate as standard (2 μM solution in 0.05 M sulfuric acid, Φ = 0.546).
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19. Related arguments can be advanced to explain the differences in binding strength between receptors 1, 2, and 3. Sensor 2 contains a sulfonic acid residue that increases the acidity of the sulfonamide NH and, relative to 1, its presumed efficacy as a hydrogen bond donor. Likewise, the presence of two ancillary hydrogen bond donors in the thiourea moiety is expected to increase the general anion binding efficiency of 3.
20. Sensing efficiency as used here is a qualitative term meant to imply improvements in a range of desirable features including linear response of the sensors to the presence of anions and a higher degree of quenching at lower anion concentrations.