Conformationally restricted aza-bodipy: A highly fluorescent, stable, near-infrared-absorbing dye

Angewandte Chemie - International Edition

Volumn 44, Issue 11, 2005, Pages 1677-1679

  Zhao, Weili ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Dyes pigments; Fluorescence; Fluorescent probes; Imaging agents

Indexed keywords

CHROMOPHORES; CONFORMATIONS; ELECTROMAGNETIC WAVE ABSORPTION; FLUORESCENCE; INFRARED RADIATION; SOLVENTS;

AZA-DIPYRROMETHANE DYE; BIOLOGICAL PROBES; NEAR-INFRARED (NIR) REGION;

AZO DYES;

4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; FLUORESCENT DYE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; NEAR INFRARED SPECTROSCOPY;

AZA COMPOUNDS; BORON COMPOUNDS; FLUORESCENT DYES; SPECTROSCOPY, NEAR-INFRARED;

EID: 17144403523     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461868     Document Type: Article

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44. Fluorescence quantum yield measurements were performed on a Fluorolog-3 instrument (Model FL-3-22) equipped with an R928P photomultiplier tube which is sensitive up to ≈ 850 nm. To obtain accurate excitation spectra, the excitation monochromator was calibrated by a xenon-lamp scan. The emission monochromator was calibrated using a water Raman scan. The response of the detector was calibrated with a standard tungsten-halogen lamp. Fluorescence quantum yield determination was performed following the method recommended by the manufacturer of the fluorometer (see: www.jobinyvon.com/ usadivisions/Fluorescence/applications/quantumyieldstrad.pdf), and was compared with other reported methods (S. Fery-Forgues, D. Lavabre, J. Chem. Educ. 1999, 76, 1260). Compound 3 was used as standard, and the measurements were performed under identical conditions to those with 1. Nondegassed, spectroscopic-grade chloroform and a 10-mm quartz cuvette were used. Very dilute solutions (A ≤ 0.010) were used to minimize reabsorption effects. The optical densities of solutions of 1 and 3 were adjusted to 0.200 at 670 nm, and these solutions were diluted by factors of 20, 40, 60, 80, and 100. The excitation wavelength was 670 nm for both compound 1 and reference 3, and a 510-nm cutoff optical filter was placed between the excitation monochromator and sample cuvette to eliminate UV (335 nm) excitation. The fluorescence quantum yield of compound 1 was calculated to be 0.278 relative to the reference (0.36), which is comparable to the data obtained by the traditional method (0.284 ± 0.006).
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