Tunable benzothiadiazole-based donor–acceptor materials for two-photon excited fluorescence

Paisley, Nathan R.; Tonge, Christopher M.; Mayder, Don M.; Thompson, Kyle A.; Hudson, Zachary M.

doi:10.1039/c9qm00627c

Cited by 18 publications

(21 citation statements)

References 55 publications

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“…Photoluminescent organic compounds and transition metal complexes with organic ligands are important components in various scientific applications, including optoelectronics, photocatalysis, and photodynamic therapy. Heteroaromatic units, in particular 2,1,3-benzothiadiazole (btd) derivatives, are often used as building blocks of optical materials [1][2][3]. Generally, btd acts as an acceptor in polymer molecules [4,5].…”

Section: Introductionmentioning

confidence: 99%

“…In this context, P,N-containing ligands are highly attractive, as they combine both strong and weak Lewis base centers. A number of btd derivatives bearing N-donor functional groups were recently studied [2,[10][11][12][13]. Phosphorus-containing btds are much less abundant; they are mainly limited to derivatives with phosphate groups [14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Structural and Photophysical Properties of 2,1,3-Benzothiadiazole-Based Phosph(III)azane and Its Complexes

et al. 2020

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Here we describe the synthesis of a novel N,N’-bis(2,1,3-benzothiadiazol-4-yl)-1-phenylphosphanediamine (H2L) and its zinc (II) and copper (I) coordination compounds [Zn2L2]·nC7H8 (1·nC7H8), [Zn2(H2L)2Cl4]·nC7H8 (2·nC7H8), and [Cu(H2L)Cl]n·nTHF (3·THF). According to single crystal X-ray diffraction analysis, H2L ligand and its deprotonated species exhibit different coordination modes. An interesting isomerism is observed for the complexes [Zn2(H2L)2Cl4] (2a and 2b) that differ by the arrangement of H2L. Both complexes possess internal cavities capable of incorporating toluene molecules. Upon toluene release, the geometry of 2b changes substantially, while that of 2a changes slightly. Due to the diverse structures, the compounds 1–3 reveal different photophysical properties. These results are discussed based on previously reported studies and DFT (density functional theory) calculations.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural and Photophysical Properties of 2,1,3-Benzothiadiazole-Based Phosph(III)azane and Its Complexes

et al. 2020

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“…47 In order to obtain the polymers with longwavelength emission, BT is used as the electron acceptor to tune emission wavelength due to its stable ICT, large Stokes shift, and bright emission. 48 Notably, PT is chosen as the energy donor and specific ClO − -sensitive unit to construct allin-one polymers, which is attributed to the following facts. The N and S atoms in PT molecule can endow PT with superior electron-donating ability, while the thioether can be specifically oxidized into the electron-withdrawing unit, sulfoxide structure, by ClO − .…”

Section: Resultsmentioning

confidence: 99%

General Strategy to Achieve Color-Tunable Ratiometric Two-Photon Integrated Single Semiconducting Polymer Dot for Imaging Hypochlorous Acid

Zhang

Dai

et al. 2021

ACS Nano

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It is highly desired and challenging to construct integrated (all-in-one) single semiconducting-polymer-derived dot (Pdot) without any postmodification but with desired performances for bioapplications. In this work, eight hypochlorous acid (HClO)-sensitive integrated polymers and corresponding polymer-derived Pdots are designed through molecular engineering to comparatively study their analytical performances for detecting and imaging HClO. The optimized polymers-derived Pdots are obtained through regulating donor–acceptor structure, the content of HClO-sensitive units, and the position of HClO-sensitive units in the polymer backbone. The designed Pdots display distinguished characteristics including multicolours with blue, yellow, and red three primary fluorescence colors, determination mode from single-channel to dual-channel (ratiometric) quantification, ultrafast response, low detection limit, and high selectivity for ClO– sensing based on specific oxidation of ClO–-sensitive unit 10-methylphenothiazine (PT) accompanied by altering the intramolecular charge transfer (ICT) and fluorescence resonance energy transfer (FRET) processes in Pdots. The prepared integrated Pdots are also applied for two-photon ClO– imaging in HeLa cells and one- and two-photon ClO– imaging produced in acute inflammation in mice with satisfactory results. We believe that the present study not only provides excellent integrated fluorescent nanoprobes for ClO– monitoring in living systems but also extends a general strategy for designing integrated semiconducting polymers and Pdots with desired performances for biological applications.

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“…Though functionalization of the BFC framework with hydrophilic groups may improve aqueous solubility, TADF materials typically exhibit strong solvatochromism, such that high‐polarity solvents such as water can red‐shift and broaden emission spectra while also reducing Φ PL . Alternatively, hydrophobic dyes can be incorporated into water‐soluble nanoparticles, removing the need for elaborate chemical functionalization [16] . For example, BFC materials have been loaded into porous silica nanoparticles or bovine serum albumin as water‐soluble matrices [17, 18] .…”

Section: Introductionmentioning

confidence: 99%

Near‐Infrared‐Emitting Boron‐Difluoride‐Curcuminoid‐Based Polymers Exhibiting Thermally Activated Delayed Fluorescence as Biological Imaging Probes

et al. 2021

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Near‐infrared‐emitting polymers were prepared using four boron‐difluoride‐curcuminoid‐based monomers using ring‐opening metathesis polymerization (ROMP). Well‐defined polymers with molecular weights of ≈20 kDa and dispersities <1.07 were produced and exhibited near‐infrared (NIR) emission in solution and in the solid state with photoluminescence quantum yields (ΦPL) as high as 0.72 and 0.18, respectively. Time‐resolved emission spectroscopy revealed thermally activated delayed fluorescence (TADF) in polymers containing highly planar dopants, whereas room‐temperature phosphorescence dominated with twisted species. Density functional theory demonstrated that rotation about the donor–acceptor linker can give rise to TADF, even where none would be expected based on calculations using ground‐state geometries. Incorporation of TADF‐active materials into water‐soluble polymer dots (Pdots) gave NIR‐emissive nanoparticles, and conjugation of these Pdots with antibodies enabled immunofluorescent labeling of SK‐BR3 human breast‐cancer cells.

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Tunable benzothiadiazole-based donor–acceptor materials for two-photon excited fluorescence

Abstract: Spectrally tunable, two-photon active benzothiadiazole-based fluorescent materials are realized by a simple synthetic strategy. Deep red emission from two-photon absorption, and incorporation into water-soluble polymer dots are achieved.

Cited by 18 publications

References 55 publications

Structural and Photophysical Properties of 2,1,3-Benzothiadiazole-Based Phosph(III)azane and Its Complexes

Structural and Photophysical Properties of 2,1,3-Benzothiadiazole-Based Phosph(III)azane and Its Complexes

General Strategy to Achieve Color-Tunable Ratiometric Two-Photon Integrated Single Semiconducting Polymer Dot for Imaging Hypochlorous Acid

Near‐Infrared‐Emitting Boron‐Difluoride‐Curcuminoid‐Based Polymers Exhibiting Thermally Activated Delayed Fluorescence as Biological Imaging Probes

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