An oxo-bacteriochlorin derivative for long-wavelength fluorescence ratiometric alcohol sensing

Abstract

A fluorescent ratiometric optical chemical sensor (optode) for alcohol detection is presented. A lipophilized bacteriochlorin derivative possessing a trifluoroacetyl group at the 3-position was synthesized for alcohol detection. When embedded in a plasticized poly(vinyl chloride) (PVC) membrane, the fluororeceptor shows a significant signal change on exposure to aqueous ethanol solutions both in the absorbance and the fluorescence emission. This optode allows the determination of ethanol concentrations in aqueous sample solutions by ratiometric fluorometry. The fluorescent indicator responds with increasing fluorescence around 701 nm and decreasing fluorescence around 751 nm towards the presence of ethanol. The optode response was found to be fully reversible in a dynamic measurement range from 0.3% to at least 25% (v/v) ethanol. The limit of detection (LOD) and the limit of quantification (LOQ) of the sensor for ethanol were estimated to be 0.1% and 0.4% (v/v), respectively. These results indicate that the new optode can be employed as an ethanol-sensing device with high sensitivity for beverage and industrial analyses.

Bacteriochlorins with a Twist: Discovery of a Unique Mechanism to Red-Shift the Optical Spectra of Bacteriochlorins

“…Bacteriochlorins possess characteristic three-band absorption spectra, including a high-intensity Soret feature (B band) and two spectrally distinct Q bands, Q x and Q y , whereby the longest absortion band Q y band (also referred to as the λ max band) lies well above 700 nm . Because bacteriochlorins absorb strongly within the spectroscopic window of tissue (the range between ∼700 and well above 1000 nm; light of 735 nm possesses the deepest penetration depth in tissue), significant efforts have been devoted to the synthesis and spectral modulation of bacteriochlorins for their utilization as photochemotherapeutics, imaging agents, or optical labels. , The NIR absorption properties can also be beneficial for their utility as chemosensors or light-harvesters . An understanding of the conformational modulation of the electronic properties of bacteriochlorins is therefore of broad interest.…”

Chromene-Annulated Bacteriochlorins

“…Because of their NIR absorbance properties, their use in light-harvesting systems is appealing . They have also been utilized in chemosensing systems …”

“…6 They have also been utilized in chemosensing systems. 7 Synthetic bacteriochlorins can be prepared in semisynthetic approaches using naturally occurring tetrapyrroles, they can be made by total syntheses, and they can be accessed by conversion of synthetic porphyrins. 4 Semisynthetic approaches are well-established, 5a,e,8 but access to chemically more stable bacteriochlorins, the desire for better synthetic handles to finetune the chromophore, or production of regio-and stereochemically well-defined molecules requires fully synthetic approaches.…”

A FRET system built on quartz plate as a ratiometric fluorescence sensor for mercury ions in water

“…Ratiometric detection, 9,10 which involves the simultaneous measurement of two fluorescence signals at different wavelengths followed by calculation of their intensity ratio, could eliminate the above-mentioned adverse effects on fluorescence signals and give greater precision to the data analysis relative to single-channel detection. [11][12][13][14][15][16][17][18][19][20][21] Conventionally, FRET-based ratiometric sensing systems have been designed in the form of small-molecular dyads which contain two fluorophores connected by a spacer through covalent links. [22][23][24] Recently, it has been found that the FRET systems can also be built within colloidal particles, such as quantum dots, [25][26][27][28] inorganic particles [29][30][31][32] and polymer particles.…”