A Versatile Photochromic Dithienylethene-Containing β-Diketonate Ligand: Near-Infrared Photochromic Behavior and Photoswitchable Luminescence Properties upon Incorporation of a Boron(III) Center

Poon, Chun‐Ting; Lam, Wai Han; Wong, Hok‐Lai; Yam, Vivian Wing‐Wah

doi:10.1021/ja105537j

Cited by 185 publications

(106 citation statements)

References 29 publications

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“…Despite the fact that photochromic switching at a boron core remains rare [36][37][38][39], there do exist several examples of photochromic systems which incorporate organoboron subunits to act as modulators of various chemical properties [40][41][42]. In particular, -BMes 2 substitution has proven to be an effective strategy for controlling the color and state-switching of DTEs via the introduction/removal of fluoride ions (F − ), which bind strongly to three-coordinated boron atoms and disrupt the π-conjugation of the molecule [43][44][45].…”

Section: Four-state Color Switchingmentioning

confidence: 99%

Isomerization and rearrangement of boriranes: from chemical rarities to functional materials

Mellerup

Wang

2018

Sci. China Mater.

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Stimuli responsive materials have recently been the subject of tremendous research efforts owing to their numerous potential applications. Although there currently exist many different types of "smart" materials, those based on photoresponsive transformations are especially attractive. In this review, we focus on a relatively new class of photochromic molecules based on the photochemistry of chelate organoborates, which form intensely colored, base-stabilized boriranes. Recent efforts to exploit the reactivity of these systems are summarized, and future prospects in materials science discussed.

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Section: Four-state Color Switchingmentioning

confidence: 99%

Isomerization and rearrangement of boriranes: from chemical rarities to functional materials

Mellerup

Wang

2018

Sci. China Mater.

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“…In addition, a photo-responsive ketoiminate was obtained using a dithienylethene unit. 35,36 The electronic structures could be altered by photo-irradiation, leading to the expression of photochromic behaviors (Scheme 3). By introducing the functional groups directly onto the boron atom in the diketonate complexes, these characteristics could be modulated.…”

Section: Building Blocks For Constructing Nanostructures and Supramolmentioning

confidence: 99%

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

2015

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The synthesis and application of organoboron complexes are a highly relevant topic owng to their unique characteristics. Based on their emissive properties, these complexes have been used to make novel optical materials and devices; boron β-diketonate is a simple and robust organoboron complex. From a series of recent studies, unique and versatile optical properties have been reported. In this review, we introduce the results of primarily recent studies on boron diketonate and related compounds containing polymers and particularly explain their optical properties. Initially, the multi-emission of boron diketonate derivatives and its application to biotechnology are explained. Next, the formation of nanostructures and its emission properties are demonstrated. The modulation of optical properties by mechanical stress is also presented. Finally, recent progress in the development of solid-emissive materials are shown with boron diketonates and their derivatives, which have aggregation-induced emission properties. The versatility of boron diketonates as a building block for the preparation of functional optical materials is the focus of this review.

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“…13,14 Various types of BF 2 fluorescent materials have been prepared, including β-diketiminate (NBN), 15,16 β-ketoiminate (NBO), 17–21 and β-diketonate (OBO) complexes. 22–24 Difluoroboron can also act as an electron-accepting group, inducing a strong dipole upon excitation, making the dyes sensitive to solvent and media polarity. 25–27 Difluoroboron β-diketonates (BF 2 bdks) are particularly interesting because of their exceptional luminescent properties in both solution and solid states.…”

Section: Introductionmentioning

confidence: 99%

Oxygen Sensing Difluoroboron Dinaphthoylmethane Polylactide

et al. 2015

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Dual emissive luminescence properties of solid-state difluoroboron β-diketonate-poly(lactic acid) (BF2bdk-PLA) materials have been utilized as biological oxygen sensors. Dyes with red-shifted absorption and emission are important for multiplexing and in vivo imaging, thus hydroxyl-functionalized dinaphthoylmethane initiators and dye-PLA conjugates BF2dnm(X)PLA (X = H, Br, I) with extended conjugation were synthesized. The luminescent materials show red-shifted absorbance (~435 nm) and fluorescence tunability by molecular weight. Fluorescence colors range from yellow (~530 nm) in 10 – 12 kDa polymers to green (~490 nm) in 20 – 30 kDa polymers. Room-temperature phosphorescence (RTP) and thermally activated delayed fluorescence (TADF) are present under a nitrogen atmosphere. For the iodine-substituted derivative, BF2dnm(I)PLA, clearly distinguishable fluorescence (green) and phosphorescence (orange) peaks are present, making it ideal for ratiometric oxygen-sensing and imaging. Bromide and hydrogen analogues with weaker relative phosphorescence intensities and longer phosphorescence lifetimes can be used as highly sensitive, concentration independent, lifetime-based oxygen sensors or for gated emission detection. BF2dnm(I)PLA nanoparticles were taken up by T41 mouse mammary cells and successfully demonstrated differences in vitro ratiometric measurement of oxygen.

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A Versatile Photochromic Dithienylethene-Containing β-Diketonate Ligand: Near-Infrared Photochromic Behavior and Photoswitchable Luminescence Properties upon Incorporation of a Boron(III) Center

Cited by 185 publications

References 29 publications

Isomerization and rearrangement of boriranes: from chemical rarities to functional materials

Isomerization and rearrangement of boriranes: from chemical rarities to functional materials

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

Oxygen Sensing Difluoroboron Dinaphthoylmethane Polylactide

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