Synthesis and investigation of BODIPYs with restricted meso-8-aryl rotation

2020 ◽  
Vol 24 (05n07) ◽  
pp. 869-877
Author(s):  
Guanyu Zhang ◽  
Maodie Wang ◽  
Caroline Ndung’U ◽  
Petia Bobadova-Parvanova ◽  
Frank R. Fronczek ◽  
...  
Keyword(s):  
Dihedral Angle ◽  
Quantum Yields ◽  
Methyl Groups ◽  
Free Rotation ◽  
Aryl Group ◽  
Chlorine Atoms ◽  
Aryl Ring ◽  
X Ray ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence

Three BODIPYs bearing 1,3,5,7-tetramethyl substituents and a meso-8-aryl group were synthesized and investigated, both experimentally and computationally. The presence of the 1,7-methyl groups and of ortho-substituents on the meso-8-aryl ring prevent free rotation of the meso-8-aryl group, resulting in high fluorescence quantum yields. Substitution at the 2,6-positions of these BODIPYs with chlorine atoms causes pronounced red-shifted absorptions and emissions, and in the case of 2,6-dichloro-1,3,5,7-tetramethyl-8-(2,4,6-triphenylphenyl)-BODIPY 2c increases its fluorescence quantum yields to 0.93 in dichloromethane and 0.98 in toluene. The X-ray structure of 1,3,5,7-tetramethyl-8-(2,4,6-triphenylphenyl)-BODIPY shows increased deviation from planarity and smaller dihedral angle of the meso-8-aryl group compared with the meso-8-phenyl- and meso-8-mesityl-BODIPY analogs. The presence of 2,6-chlorine atoms was found to not significantly affect the rotational barriers of the meso-8-aryl-groups.

Regioselective Oxidative Cross-Coupling Reaction: Synthesis of Imidazo[1,2-a]pyridine Fluorophores

Synthesis ◽  
2021 ◽  
Author(s):  
Xianglong Chu ◽  
Yadi Niu ◽  
Chen Ma ◽  
Xiaodong Wang ◽  
Yunliang Lin ◽  
...  
Keyword(s):  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reaction ◽  
Color Tunable ◽  
Palladium Catalyzed ◽  
Structure Relationship ◽  
High Fluorescence

AbstractA rapid access to a series of N-heteroarene fluorophores has been developed on the basis of the palladium-catalyzed direct oxidative C–H/C–H coupling of imidazo[1,2-a]pyridines with thiophenes/furans. The photophysical properties–structure relationship was systematically investigated. The resulting N-heteroarene fluorophores present color-tunable emissions (λem: 431–507 nm in CH2Cl2) and high fluorescence quantum yields (up to 91% in CH2Cl2).

The Molecular Geometry of Diastereoisomeric Bis[α-(9-anthryl)ethyl] Ethers

1985 ◽  
Vol 38 (9) ◽  
pp. 1417 ◽  
Author(s):  
H Becker ◽  
VA Patrick ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Least Squares ◽  
Dihedral Angle ◽  
Molecular Geometry ◽  
Dihedral Angles ◽  
Methyl Groups ◽  
X Ray Diffraction ◽  
X Ray ◽  
Meso Form ◽  
Aromatic Systems

The crystal structures of racemic bis [α-(9-anthryl)] ether and its meso form have been determined by single-crystal X-ray diffraction methods at 295 K, being refined by least squares to residuals of 0.053 and 0.041 for 1868 and 3568 independent 'observed' reflections respectively. Crystals of the racemate are orthorhombic, Pcab, a 23.07(1), b 19.85(2), c 10.241(8) Ǻ, Z 8. Crystals of the meso form are triclinic, Pī , a 19.032(12), b 14.207(11), c 9.451(8) Ǻ, α 79.46(6), β 89.68(6), γ 68.97(5)°, Z 4. In the racemate , the dihedral angle between the methyl groups along the ether bonds is 12°, and the short axes of the anthracene moieties lie at an angle of about 120°. In the meso compound, for the two molecules the dihedral angles between the methyl groups along the ether bonds are 90 and 93°, the angle between the two anthracene moieties is 90°, and the interplanar angles between the partly overlapping aromatic systems are 46 and 43°.

scholarly journals Photoluminescence in m-carborane–anthracene triads: a combined experimental and computational study

2018 ◽  
Vol 6 (42) ◽  
pp. 11336-11347 ◽  
Author(s):  
Mahdi Chaari ◽  
Zsolt Kelemen ◽  
José Giner Planas ◽  
Francesc Teixidor ◽  
Duane Choquesillo-Lazarte ◽  
...  
Keyword(s):  
Computational Study ◽  
Fluorescence Emission ◽  
Fluorescence Properties ◽  
Quantum Yields ◽  
Aggregate State ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence

m-Carborane has demonstrated to be a perfect platform to boost the fluorescence properties of anthracene, giving rise to high fluorescence quantum yields in solution and also retaining fluorescence emission in the aggregate state.

scholarly journals Bis(diarylethenyl)-thiophenes, -bithiophenes, and -terthiophenes: a new series of electrochromic systems that exhibit a fluorescence response

2017 ◽  
Vol 95 (3) ◽  
pp. 243-252 ◽  
Author(s):  
Yusuke Ishigaki ◽  
Hidetoshi Kawai ◽  
Ryo Katoono ◽  
Kenshu Fujiwara ◽  
Hiroki Higuchi ◽  
...  
Keyword(s):  
Alkyl Chain ◽  
Alkyl Chain Length ◽  
Electron Donors ◽  
Quantum Yields ◽  
Redox Potentials ◽  
Aryl Group ◽  
Electrochromic Materials ◽  
Fluorescence Response ◽  
Fluorescence Quantum Yields ◽  
Electrochromic Systems

2,5-Bis(diarylethenyl)thiophenes (1) and their bithiophene (2) and terthiophene (3) homologues were designed as a new series of violene/cyanine-hybrid-type electrochromic materials. Alkoxyphenyl and dialkylaminophenyl groups are used as the aryl group in the cyanine parts of 1/2/3O and 1/2/3N, respectively, which emit fluorescence in the neutral state but not in the oxidized state. Voltammetric analyses of 18 newly prepared electron donors show that they all undergo two reversible one-electron oxidations. Redox potentials, UV–vis spectral features, and fluorescence quantum yields are important parameters for characterizing the present electrochromic behavior with a fluorescence response, and can be finely tuned by changing aryl groups in the cyanine part, the number of thiophene rings in the violene part, and the alkyl-chain length of the alkoxyphenyl or diaklylaminophenyl groups (R = CH3, C8H17, C16H33), which makes this a versatile platform for the design of novel electrochromic materials.

Alkynylpyrenes as Improved Pyrene-Based Biomolecular Probes with the Advantages of High Fluorescence Quantum Yields and Long Absorption/Emission Wavelengths

2006 ◽  
Vol 12 (3) ◽  
pp. 824-831 ◽  
Author(s):  
Hajime Maeda ◽  
Tomohiro Maeda ◽  
Kazuhiko Mizuno ◽  
Kazuhisa Fujimoto ◽  
Hisao Shimizu ◽  
...  
Keyword(s):  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence

SYNTHESIS, FLUORESCENCE AND ELECTROCHEMICAL PROPERTIES OF SYMMETRICAL CHROMOPHORES WITH ELECTRON ACCEPTING OXADIAZOLE

2008 ◽  
Vol 17 (04) ◽  
pp. 473-485 ◽  
Author(s):  
XIAOQIN ZHU ◽  
YING QIAN ◽  
WEI HUANG ◽  
CHANGGUI LU ◽  
YIPING CUI
Keyword(s):  
Single Photon ◽  
Quantum Yields ◽  
Compound I ◽  
Central Wavelength ◽  
Good Thermal Stability ◽  
Fluorescence Quantum Yields ◽  
Two Photon ◽  
Homo And Lumo ◽  
High Fluorescence ◽  
Compound Ii

Two symmetrical TPA chromophores containing 1,3,4-oxadiazole group were designed and synthesized through the Wittig–Horner reaction. All compounds were characterized by NMR, IR, UV and melting point. Chromophore I and II showed good thermal stability and did lose less than 5% weight on heating to about 300°C. The electrochemical property was explored by cyclic voltammetry. The HOMO and LUMO energy of compound I were estimated to be -3.65 eV and -1.09 eV. That of compound II were -3.69 eV and -1.10 eV. Both chromophores exhibited a positive solvatochromic behavior. In CH2Cl2 , the maximum peaks of single-photon-excited fluorescence (SPEF) were at 512 nm for compound I and at 495 nm for compound II with high fluorescence quantum yields 0.73 and 0.70, respectively. The two-photon-excited fluorescence (TPEF) had also been investigated. Pumped by femtosecond laser at 800 nm, strong up-conversion emissions with the central wavelength were at 532 nm for compound I and 550 nm for compound II in the solution of CH2Cl2 .

High-Quality Water-Soluble Core/Shell/Shell CdSe/CdS/ZnS Quantum Dots Balanced by Ionic and Nonionic Hydrophilic Capping Ligands

NANO ◽  
2016 ◽  
Vol 11 (07) ◽  
pp. 1650073 ◽  
Author(s):  
Lu Liu ◽  
Hu Xu ◽  
Bing Shen ◽  
Xinhua Zhong
Keyword(s):  
Quantum Dots ◽  
Colloidal Stability ◽  
Water Soluble ◽  
Quantum Yields ◽  
Surface Charges ◽  
Fluorescence Quantum Yields ◽  
Carboxylic Groups ◽  
Potential Applications ◽  
High Fluorescence ◽  
Capping Ligands

Pentaerythritol tetrakis 3-mercaptopropionate (PTMP) grafted poly(acryl acid) (PAA) ionic hydrophilic oligomer PAA-PTMP (PP) and dihydrolipoic acid (DHLA) grafted methoxypoly(ethylene glycol) (mPEG) nonionic hydrophilic oligomer mPEG-DHLA (PD) have been designed, synthesized and used as co-capping ligands in water-solubilization of hydrophobic quantum dots (QDs) via ligand exchange. The obtained oligomers with multi-thiol groups could bind strongly to the surface atoms of QDs. Meanwhile, the carboxyl groups (from PP) and mPEG segment (from PD) can render QDs water-soluble, and the free carboxylic groups can possibly be used for the further bioconjugation. The resulting water-soluble QDs have been characterized by ultraviolet-visible (UV-Vis), fluorescence, Fourier transform infrared (FTIR) spectroscopy as well as transmission electron microscopy (TEM) and dynamic light scattering (DLS) techniques. The water-soluble QDs have relatively small hydrodynamic size (10[Formula: see text]12 nm), and importantly, retain high fluorescence quantum yields (up to 45%) compared with that of the originally hydrophobic QDs (49%). In addition, they have tunable surface charges and show excellent colloidal stability over a relatively broad pH range ([Formula: see text]), in high salt concentration, and even after thermal treatment at 100[Formula: see text]C. These results indicate that the water-soluble QDs coated by PP and PD oligomers have potential applications in cellular imaging and biosensor.

scholarly journals Towards Mycobacterium tuberculosis detection at the point-of-care: a brighter solvatochromic probe permits the detection of mycobacteria within minutes

2020 ◽  
Author(s):  
Mireille Kamariza ◽  
Samantha G. L. Keyser ◽  
Ashley Utz ◽  
Benjamin D. Knapp ◽  
Green Ahn ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Fluorescence Intensity ◽  
Point Of Care ◽  
Fold Increase ◽  
Diagnostic Methods ◽  
Quantum Yields ◽  
Low Resource Settings ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence ◽  
Solvatochromic Dye

ABSTRACTThere is an urgent need for point-of-care tuberculosis (TB) diagnostic methods that are fast, inexpensive, and operationally simple. Here, we report on a bright solvatochromic dye trehalose conjugate that specifically detects Mycobacterium tuberculosis (Mtb) in minutes. 3-hydroxychromone (3HC) dyes, known to yield high fluorescence quantum yields, exhibit shifts in fluorescence intensity in response to changes in environmental polarity. We synthesized two analogs of 3HC-trehalose conjugates (3HC-2-Tre and 3HC-3-Tre) and determined that 3HC-3-Tre has exceptionally favorable properties for Mtb detection. 3HC-3-Tre-labeled mycobacterial cells displayed a 10-fold increase in fluorescence intensity compared to our previously reports on the dye 4,4-N,N-dimethylaminonapthalimide (DMN-Tre). Excitingly, we detected fluorescent Mtb cells within 10 minutes of probe treatment. Thus, 3HC-3-Tre permits rapid visualization of mycobacteria that ultimately could empower improved Mtb detection at the point-of-care in low-resource settings.

scholarly journals Utilizing selective chlorination to synthesize new triangulenium dyes

2021 ◽  
Author(s):  
Jesper Dahl Jensen ◽  
Niels Bisballe ◽  
Laura Kacenauskaite ◽  
Maria Storm Thomsen ◽  
Junsheng Chen ◽  
...  
Keyword(s):  
Early Stage ◽  
Quantum Yields ◽  
Electrophilic Aromatic Substitution ◽  
Fluorescence Lifetimes ◽  
Aromatic Substitution ◽  
Compound A ◽  
Fluorescence Quantum Yields ◽  
Reduction Potentials ◽  
Snar Reaction ◽  
High Fluorescence

Access to functionalization of new sites on the triangulenium core structure has been achieved at an early stage by chlorination with N-chlorosuccinimide (NCS), giving rise to two new triangulenium dyes (1 and 2). By introducing the chlorine functionalities in the acridinium precursor, positions complementary to those previously accessed by electrophilic aromatic substitution of the final dyes can be accesed. The chlorination is selective, giving only one regioisomer for both mono- and dichlorination products. For the monochlorinated acridinium compound a highly selective ring-closing reaction was discovered to generate only a single regioisomer of the cationic [4]helicene product. This discovery aspired further investigations into the mechanism of [4]helicene formation and to the first isolation of the previously proposed intermediate of the two-step SNAr reaction, key to all aza-bridged triangulenium and helicenium systems. A late stage functionalization of DAOTA+ with NCS gave rise to a different dichlorinated compound (2). The fully ring closed chlorinated triangulenium dyes 1, 2 and 3 show a redshift in absorption and emission relative to the non-chlorinated analogues, while still maintaining relatively high fluorescence quantum yields of 36%, 26%, and 41%, and long fluorescence lifetimes of 15 ns, 12.5 ns and 16 ns, respectively. Cyclic voltammetry shows that chlorination of the triangulenium dyes significantly lowers reduction potentials and thus allows for efficient tuning of redox and photo-redox properties.

A bright red-emitting flavonoid for Al3+ detection in live cells without quenching ICT fluorescence

2019 ◽  
Vol 55 (49) ◽  
pp. 7041-7044 ◽  
Author(s):  
Chathura S. Abeywickrama ◽  
Keti A. Bertman ◽  
Yi Pang
Keyword(s):  
Stokes Shift ◽  
Live Cells ◽  
Quantum Yields ◽  
Large Stokes Shift ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence

A bright red-emitting flavonoid derivative was synthesized, which exhibited a large Stokes shift (Δλ > 150 nm) and high fluorescence quantum yields (ϕfl = 0.10–0.35).

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