Chiral discrimination with a fluorescent boron–dipyrromethene dye

Beer, Gerhard; Rurack, Knut; Daub, Jörg

doi:10.1039/b102376b

Cited by 109 publications

(41 citation statements)

References 26 publications

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“…Whereas the fluorescence of p SAc‐ 1 decays in 4.68 ns in MeCN, 1 shows a lifetime of 5.25 ns and ( o S‐ 1 ) 2 a lifetime of 6.47 ns. Similar observations have previously been made by us for a 1,1′‐binaphthyl‐appended bichromophoric BDP20a and for 2‐methoxy‐3‐BDP‐naphthalene, which show decay times of 6.17 and 6.55 ns in acetonitrile. These features are not yet completely understood, and current theoretical and experimental work is directed at more fundamental understanding.…”

Section: Resultssupporting

confidence: 88%

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

Röhr

Trieflinger

Rurack

et al. 2006

Chemistry A European J

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A luminescent molecular switch in which the active thiol/disulfide switching element is attached to a meso-phenyl-substituted boron-dipyrromethene (BDP) chromophore as the signalling unit is presented. The combination of these two functional units offers great versatility for multimodal switching of luminescence: 1) deprotonation/protonation of the thiol/thiolate moiety allows the highly fluorescent meso-p-thiophenol-BDP and its nonfluorescent thiolate analogue to be chemically and reversibly interconverted, 2) electrochemical oxidation of the monomeric dyes yields the fluorescent disulfide-bridged bichromophoric dimer, also in a fully reversible process, and 3) besides conventional photoexcitation, the well separated redox potentials of the BDP also allow the excited BDP state to be generated electrochemically (i.e., processes 1) and 2) can be employed to control both photo- and electrochemiluminescence (ECL) of the BDP). The paper introduces and characterizes the various states of the switch and discusses the underlying mechanisms. Investigation of the ortho analogue of the dimer provided insight into potential chromophore-chromophore interactions in such bichromophoric architectures in both the ground and the excited state. Comparison of the optical and redox properties of the two disulfide dimers further revealed structural requirements both for redox switches and for ECL-active molecular ensembles. By employing thiol/disulfide switching chemistry and BDP luminescence features, it was possible to create a prototype molecular ensemble that shows both fully reversible proton- and redox-gated electrochemiluminescence.

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Section: Resultssupporting

confidence: 88%

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

Röhr

Trieflinger

Rurack

et al. 2006

Chemistry A European J

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“…Functional dyes that rely on the parent BODIPY chromophore ( 1 , 1) show absorption maxima between 495 and 525 nm and emission maxima between 505 and 545 nm 5,6 . Bathochromic shifts of the optical transitions have been realized by the following:…”

Section: Chemical Modification Strategies Toward Long‐wavelength Bodimentioning

confidence: 99%

Red/Near‐infrared Boron–Dipyrromethene Dyes as Strongly Emitting Fluorophores

Descalzo

Shen

et al. 2008

Annals of the New York Academy of Sciences

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We present an overview of the state of the art in long-wavelength boron-dipyrromethene (BODIPY) fluorophores, focusing on strategies to shift the absorption and emission bands into the red/near-infrared (NIR) range of the spectrum. This report also discusses chemical modifications of the chromophoric core to obtain analyte-responsive fluorophores, including examples of pH and metal ion indicators. Finally, we present a new series of phenanthrene-fused BODIPY dyes, emitting with high efficiency in the red/NIR region of the spectrum, as well as discussing potential applications thereof as probes.

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“…30,31 Recently, uorescence technology has witnessed signicant progress in examining enantiomeric compositions. 32,33 For instance, uorescent probes have attracted much attention due to their high sensitivity, rapidity, and safety in uorescence analysis. [34][35][36] In theory, a uorescent substance with chiral recognition capacity, especially those from chiral helical polymers showing chiral amplication effects, [37][38][39][40][41] shall provide promising chiral uorescent materials.…”

Section: Introductionmentioning

confidence: 99%

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

Yang

Zhao

et al. 2020

Nanoscale Adv.

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Chirality is ubiquitous in nature and closely related to the pharmacological effects of chiral drugs. Therefore, chiral recognition of molecular enantiomers becomes an important research theme. Fluorescence detection is highly sensitive and fast but has achieved only limited success in enantiomeric detection due to the lack of powerful chiral fluorescence detection materials. In this paper, a novel chiral fluorescent probe material, i.e. a chiral fluorescent nanofiber membrane, is prepared from chiral helical substituted polyacetylene by the electrospinning technique. The SEM images demonstrate the success in fabricating continuous, uniform nanofibers with a diameter of about 100 nm. Circular dichroism spectra show that the nanofibers exhibit fascinating optical activity. One of the enantiomeric chiral fluorescent membranes has chiral fluorescence recognition effects towards alanine and chiral phenylethylamine, while the other enantiomeric membrane does not. The prepared chiral fluorescent nano-materials are expected to find various applications in chirality-related fields due to their advantages such as chirality, fluorescence, and a high specific surface area. The established preparation approach also promises a potent and versatile platform for developing advanced nanofiber materials from conjugated polymers. † Electronic supplementary information (ESI) available: Structural formula, FT-IR spectra, GPC, electrospinning parameters, SEM images, digital photo of uorescent polymer membranes, CD and UV-vis absorption spectra, and uorescence emission spectra. See

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Chiral discrimination with a fluorescent boron–dipyrromethene dye

Abstract: The optically active binaphthalene boron-dipyrromethene (BDP) conjugate 1 shows chiral discrimination towards the enantiomers of 1-phenylethylamine by distinguishable quenching rates of the BDP fluorescence.

Cited by 109 publications

References 26 publications

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

Red/Near‐infrared Boron–Dipyrromethene Dyes as Strongly Emitting Fluorophores

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

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