meso-Alkoxy BODIPYs with a good balance between larger Stokes shifts and higher fluorescence quantum yields

RSC Advances ◽  
2013 ◽  
Vol 3 (7) ◽  
pp. 2203 ◽  
Author(s):  
Lu Wang ◽  
Yuhui Zhang ◽  
Yi Xiao
Keyword(s):  
Quantum Yields ◽  
Good Balance ◽  
Fluorescence Quantum Yields ◽  
Stokes Shifts

Chlorination vs. fluorination: a study of halogenated benzo[c][1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging

2020 ◽  
Vol 44 (19) ◽  
pp. 7740-7748
Author(s):  
Daize Mo ◽  
Li Lin ◽  
Pengjie Chao ◽  
Hanjian Lai ◽  
Qingwen Zhang ◽  
...  
Keyword(s):  
Near Infrared ◽  
Cellular Imaging ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Stokes Shifts

The chlorinated dots based on chlorinated benzo[c][1,2,5]thiadiazole unit possess higher fluorescence quantum yields, larger Stokes shifts, and better photostability than the fluorinated dots.

Synthesis and Photophysical Properties of 3-(Trifluoromethyl)-2H-imidazo[5,1-a]isoquinolinium Chloride Derivatives

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 296-300 ◽  
Author(s):  
Ali Darehkordi ◽  
Fariba Rahmani ◽  
Mahin Ramezani ◽  
Alireza Bazmandegan-Shamili
Keyword(s):  
Blue Light ◽  
Uv Radiation ◽  
Photophysical Properties ◽  
Molecular Probes ◽  
Quantum Yields ◽  
Light Emitting ◽  
Fluorescence Studies ◽  
Fluorescence Quantum Yields ◽  
Fluorescent Molecular Probes ◽  
Stokes Shifts

A series of novel blue-light-emitting 2H-imidazo[5,1-a]isoquinolinium chloride derivatives were synthesized by the reaction of isoquinoline with trifluoroacetimidoyl chlorides and isocyanides in dry CH2Cl2 in excellent yields. Fluorescence studies showed that the compounds absorb UV radiation and then emit blue light at about 481 nm with moderate to good fluorescence quantum yields. These compounds also showed high Stokes shifts, and can be used to develop ­ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

scholarly journals Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

2016 ◽  
Vol 12 ◽  
pp. 2055-2064 ◽  
Author(s):  
Dominik Urselmann ◽  
Konstantin Deilhof ◽  
Bernhard Mayer ◽  
Thomas J J Müller
Keyword(s):  
Cyclic Voltammetry ◽  
Helical Structure ◽  
Quantum Yields ◽  
Absorption Bands ◽  
One Pot ◽  
Fluorescence Quantum Yields ◽  
Oxidation Potentials ◽  
Td Dft ◽  
Lower Oxidation ◽  
Stokes Shifts

The pseudo five-component Sonogashira–Glaser cyclization synthesis of symmetrically 2,5-diaryl-substituted thiophenes is excellently suited to access thienyl-bridged oligophenothiazines in a one-pot fashion. Three thienyl-bridged systems were intensively studied by UV–vis and fluorescence spectroscopy as well as by cyclic voltammetry. The oxidation proceeds with lower oxidation potentials and consistently reversible oxidations can be identified. The Stokes shifts are large and substantial fluorescence quantum yields can be measured. Computational chemistry indicates lowest energy conformers with sigmoidal and helical structure, similar to oligophenothiazines. TD-DFT and even semiempirical ZINDO calculations reproduce the trends of longest wavelengths absorption bands and allow the assignment of these transitions to possess largely charge-transfer character from the adjacent phenothiazinyl moieties to the central thienyl unit.

Synthesis and photophysical properties of meso-aryloxy linked BODIPY monomers, dimers, and trimer

2016 ◽  
Vol 20 (01n04) ◽  
pp. 475-489 ◽  
Author(s):  
Changjiang Yu ◽  
Qinghua Wu ◽  
Zhonghua Tian ◽  
Tingting Li ◽  
Erhong Hao ◽  
...  
Keyword(s):  
Photophysical Properties ◽  
Spatial Arrangement ◽  
Nucleophilic Aromatic Substitution ◽  
Quantum Yields ◽  
Aromatic Substitution ◽  
Polar Solvents ◽  
Fluorescence Quantum Yields ◽  
Species Formation ◽  
The Relationship ◽  
Stokes Shifts

A series of meso-aryloxy linked BODIPY monomers, dimers and trimer were synthesized by nucleophilic aromatic substitution (SNAr) reaction from phenols with meso-chloro BODIPY and their photophysical properties were systematically studied by UV-vis and fluorescence spectroscopy. The relationship between their photophysical properties and the spatial arrangement of meso-aryloxy linked BODIPYs has been discussed. The monomers exhibited different extent solvent-dependent fluorescence, and fluorescence quenching in polar solvents were found relative to the HOMO energies of the donor (meso-phenols), indicating possible PET effect from meso-phenols to the BODIPY fluorophore. Ortho-dimer showed unusual broad red-shifted emission bands centered at 550 nm with a larger Stokes shifts at the range of 2900–3400 cm[Formula: see text], and low fluorescence quantum yields, which was in sharp contrast to those of other dimers and trimer, indicating of possible excimeric species formation due to slipped cofacial arrangement ofortho-dimer.

Fluoreszenz von Distyrylbenzolen und Distyrylstilbenen / Fluorescence of Distyrylbenzenes and Distyrylstilbenes

1982 ◽  
Vol 37 (11) ◽  
pp. 1472-1480 ◽  
Author(s):  
R. Erckel ◽  
H. Frühbeis
Keyword(s):  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Emission Spectra ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Stokes Shifts

Absorption, corrected emission spectra, fluorescence quantum yields, and preparation are reported for distyrylbenzene, distyrylstilbene and substituted derivatives. The Stokes shifts are measured in three solvents and correlated with quantum chemical calculations.

scholarly journals A Convenient Synthesis of Diketopyrrolopyrrole Dyes

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4758
Author(s):  
Vitor A. S. Almodôvar ◽  
Augusto C. Tomé
Keyword(s):  
High Performance ◽  
Coupling Reaction ◽  
Quantum Yields ◽  
Reaction Conditions ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reaction ◽  
Convenient Synthesis ◽  
Organic Optoelectronic ◽  
High Fluorescence ◽  
Stokes Shifts

Diketopyrrolo[3,4-c]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki–Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.

Red-emitting boron difluoride complexes with a mega-large Stokes shift and unexpectedly high fluorescence quantum yield

2020 ◽  
Vol 56 (14) ◽  
pp. 2159-2162 ◽  
Author(s):  
Xiaojie Ren ◽  
Fan Zhang ◽  
Hongchen Luo ◽  
Lide Liao ◽  
Xiangzhi Song ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Fluorescence Quantum Yield ◽  
Stokes Shift ◽  
Quantum Yields ◽  
Large Stokes Shift ◽  
Fluorescence Quantum Yields ◽  
Boron Difluoride ◽  
High Fluorescence ◽  
Stokes Shifts ◽  
High Fluorescence Quantum Yield

Introduction of a tetrahydroquinoxaline donor into boron difluoride complexes largely extended their emissions (617–684 nm), highly improved their fluorescence quantum yields (up to 0.68) and greatly increased their Stokes shifts (up to 209 nm).

scholarly journals Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

2016 ◽  
Vol 12 ◽  
pp. 2739-2747 ◽  
Author(s):  
Lukas J Patalag ◽  
Daniel B Werz
Keyword(s):  
Fatty Acids ◽  
Chain Length ◽  
Fluorescent Dyes ◽  
Quantum Yields ◽  
Synthesis And Characterization ◽  
Absorption Properties ◽  
Fluorescence Quantum Yields ◽  
Degree Of Unsaturation ◽  
Stokes Shifts

Herein, we report on the synthesis and characterization of novel fluorescent fatty acids with large Stokes shifts. Three examples consisting of the same number of carbon atoms and thus of similar chain length are presented differing in their degree of unsaturation. As major fluorogenic contributor at the terminus benzo[c][1,2,5]thiadiazole was used. Respective syntheses based on Wittig reactions followed by iodine-mediated isomerization are presented. The absorption properties are modulated by the number of conjugated C=C double bonds of the oligoene chain ranging from one to three. Large Stokes shifts of about 4900–5700 cm−1 and fluorescence quantum yields of up to 0.44 were observed.

Novel Dual BODIPY-Carbazole Conjugates with Various Linkers

2017 ◽  
Vol 70 (7) ◽  
pp. 806 ◽  
Author(s):  
Qiao Zong ◽  
Hongbin Zhao ◽  
Weinan Zhou ◽  
Wentao Zhang ◽  
Junxu Liao ◽  
...  
Keyword(s):  
Energy Levels ◽  
Molecular Geometry ◽  
Quantum Yields ◽  
Visible Absorption ◽  
Fluorescence Quantum Yields ◽  
Photovoltaic Applications ◽  
Shoulder Peak ◽  
Membered Heterocycle ◽  
Homo Lumo ◽  
Stokes Shifts

Four dual BODIPY-carbazole conjugates (BDPa–d, BODIPY is 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), with various π bridges, including none, phenyl, thiophene, and furan, were designed and synthesized. The results suggest that the π bridges have significant effect on the thermal, photophysical, and electrochemical properties of the conjugates. BDPc and BDPd, with a five-membered heterocycle as a π bridge possessing more coplanar molecular geometry, exhibit broader and red-shifted absorption with an obvious charge transfer shoulder peak, as well as red-shifted emission. UV-visible absorption spectroscopy and cyclic voltammetry results show that the extension of the π-conjugated system leads to a reduction in the optical gap with a decrease of the LUMO level. All conjugates display remarkable Stokes shifts (107–216 nm) and low fluorescence quantum yields. BDPc and BDPd, which essentially possess broad and intense absorption, and suitable HOMO–LUMO energy levels, are potential candidates for light-harvesting and photovoltaic applications.

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