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1.
J Org Chem ; 89(12): 9092-9097, 2024 Jun 21.
Article in English | MEDLINE | ID: mdl-38841830

ABSTRACT

Shortwave infrared (SWIR, 1000-1700 nm) absorbing and emitting dyes are needed for infrared diodes and sensors used in a wide variety of industrial and medical applications. Herein, an electron-withdrawing phosphine oxide (P═O) substituted xanthene is coupled with strong indolizine donors to produce a SWIR absorbing (λabs = 1294 nm in DCM) and emitting (λemis = 1450 nm in DCM) dye called PRos1450. The unique properties of this dye are characterized via photophysical, electrochemical, and computational analyses.

2.
RSC Adv ; 14(13): 9254-9261, 2024 Mar 14.
Article in English | MEDLINE | ID: mdl-38505385

ABSTRACT

Latent bloodstain detection remains imperative for crime scene investigators. Widely used luminol offers high sensitivity to human blood, but can produce untrustworthy results from a bleach-cleaned crime scene or in a room not dark enough. Furthermore, dark pigments impede imaging bloodstains covered by dark materials with previously reported bloodstain detection agents. A novel on/off human albumin-sensing dye (SO3C7) is reported herein with a longer emission wavelength (942 nm) than previous materials that allows imaging behind ∼5 mm of black fabric. The switch-on emission of SO3C7 is selective and sensitive to human albumin and lasts longer than luminol (24-48 hours). Emission studies, transient absorption spectra (TAS), and near-infrared (NIR) photographs herein describe the albumin sensing properties of the dye.

3.
Spectrochim Acta A Mol Biomol Spectrosc ; 303: 123133, 2023 Dec 15.
Article in English | MEDLINE | ID: mdl-37473664

ABSTRACT

Cannabinoids, a class of molecules specific to the cannabis plant, are some of the most relevant molecules under study today due to their widespread use and varying legal status. Here, we present Raman spectra of a series of eleven cannabinoids and compare them to simulated spectra from density functional theory computations. The studied cannabinoids include three cannabinoid acids (Δ9-THC acid, CBD acid, and CBG acid) and eight neutral ones (Δ9-THC, CBD, CBG, CBDVA, CBDV, Δ8-THC, CBN and CBC). All cannabinoids have been isolated from cannabis plant gown at the University of Mississippi. The data presented in this work represents the most resolved experimental and highest-level simulated spectra available to date for each cannabinoid. All cannabinoids displayed higher peak separation in the experimental spectra than CBGA, which is most likely attributable to physical composition of the samples. The overall agreement between the experimental and simulated spectra is good, however for certain vibrational modes, especially those in the -OH stretching region, deviations are observed due to hydrogen bonding, suggesting that the OH stretching region is a good probe for decarboxylation reactions in these and related species.


Subject(s)
Cannabinoids , Cannabis , Cannabinoids/chemistry , Dronabinol , Spectrum Analysis, Raman , Density Functional Theory , Cannabis/chemistry
4.
Molecules ; 28(3)2023 Jan 29.
Article in English | MEDLINE | ID: mdl-36770954

ABSTRACT

Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700-1000 nm) and shortwave infrared (SWIR, 1000-1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible energy region. To tune these chromophores to the NIR region, fused nitrogen-based heterocyclic indolizine donors were added to a BODIPY scaffold. The indolizine BODIPY dyes were synthesized via microwave-assisted Knoevenagel condensation with indolizine aldehydes. The non-protonated dyes showed NIR absorption and emission at longer wavelengths than an aniline benchmark. Protonation of the dyes produced a dramatic 0.35 eV bathochromic shift (230 nm shift from 797 nm to 1027 nm) to give a SWIR absorption and emission (λmaxemis = 1061 nm). Deprotonation demonstrates that material emission is reversibly switchable between the NIR and SWIR.

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