AEE-active cyclic tetraphenylsilole derivatives with ∼100% solid-state fluorescence quantum efficiency

2015 ◽  
Vol 44 (29) ◽  
pp. 12970-12975 ◽  
Author(s):  
Yuanjing Cai ◽  
Kerim Samedov ◽  
Brian S. Dolinar ◽  
Haley Albright ◽  
Zhegang Song ◽  
...  
Keyword(s):  
Solid State ◽  
Quantum Efficiency ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Solid State Fluorescence

Bright tetraphenylsilole-containing cyclosiloxanes with 500 nm emission and ∼100% solid-state fluorescence quantum yields.

scholarly journals Indenopyrans – synthesis and photoluminescence properties

2016 ◽  
Vol 12 ◽  
pp. 825-834 ◽  
Author(s):  
Andreea Petronela Diac ◽  
Ana-Maria Ţepeş ◽  
Albert Soran ◽  
Ion Grosu ◽  
Anamaria Terec ◽  
...  
Keyword(s):  
Solid State ◽  
Emission Band ◽  
Fluorescence Spectra ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Band Broadening ◽  
Photoluminescence Properties ◽  
Fluorescence Quantum Yields ◽  
Blue Emitters ◽  
Solid State Fluorescence

New indeno[1,2-c]pyran-3-ones bearing different substituents at the pyran moiety were synthesized and their photophysical properties were investigated. In solution all compounds were found to be blue emitters and the trans isomers exhibited significantly higher fluorescence quantum yields (relative to 9,10-diphenylanthracene) as compared to the corresponding cis isomers. The solid-state fluorescence spectra revealed an important red shift of λmax due to intermolecular interactions in the lattice, along with an emission-band broadening, as compared to the solution fluorescence spectra.

Multicomponent reaction-based discovery of pyrimido[2,1-b][1,3]benzothiazole (PBT) as a novel core for full-color-tunable AIEgens

2021 ◽  
Author(s):  
Shan-Shan Gong ◽  
Rui Kong ◽  
Chunhong Zheng ◽  
Congbin Fan ◽  
Chengjun Wang ◽  
...  
Keyword(s):  
Solid State ◽  
Multicomponent Reaction ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Full Color ◽  
Color Tunable ◽  
Solid State Fluorescence ◽  
Color Tunability

The Hf(OTf)4-catalyzed three-component (3CR) was employed as a powerful tool for facile access to a library of 23 pyrimido[2,1-b][1,3]benzothiazole (PBT)-based AIEgens with full-color tunability, solid-state fluorescence quantum yields up to...

scholarly journals Towards Blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 445 ◽  
Author(s):  
Monika Cekaviciute ◽  
Aina Petrauskaite ◽  
Sohrab Nasiri ◽  
Jurate Simokaitiene ◽  
Dmytro Volyniuk ◽  
...  
Keyword(s):  
Solid State ◽  
Quantum Yields ◽  
Yellow Emission ◽  
Blue Color ◽  
Television System ◽  
Fluorescence Quantum Yields ◽  
Deep Blue ◽  
Wide Range ◽  
Cyano Groups ◽  
High Yields

Aiming to design blue fluorescent emitters with high photoluminescence quantum yields in solid-state, nitrogen-containing heteroaromatic 9,9-dimethylacridine was refined by tetraphenylethene and triphenylethene. Six tetra-/triphenylethene-substituted 9,9-dimethylacridines were synthesized by the Buchwald-Hartwig method with relatively high yields. Showing effects of substitution patterns, all emitters demonstrated high fluorescence quantum yields of 26–53% in non-doped films and 52–88% in doped films due to the aggregation induced/enhanced emission (AIE/AIEE) phenomena. In solid-state, the emitters emitted blue (451–481 nm) without doping and deep-blue (438–445 nm) with doping while greenish-yellow emission was detected for two compounds with additionally attached cyano-groups. The ionization potentials of the derivatives were found to be in the relatively wide range of 5.43–5.81 eV since cyano-groups were used in their design. Possible applications of the emitters were demonstrated in non-doped and doped organic light-emitting diodes with up to 2.3 % external quantum efficiencies for simple fluorescent devices. In the best case, deep-blue electroluminescence with chromaticity coordinates of (0.16, 0.10) was close to blue color standard (0.14, 0.08) of the National Television System Committee.

Highly fluorescent triazolopyridine–thiophene D–A–D oligomers for efficient pH sensing both in solution and in the solid state

2019 ◽  
Vol 21 (13) ◽  
pp. 7174-7182 ◽  
Author(s):  
Nannan Jian ◽  
Kai Qu ◽  
Hua Gu ◽  
Lie Zou ◽  
Ximei Liu ◽  
...  
Keyword(s):  
Solid State ◽  
Fluorescence Quenching ◽  
Quantum Yields ◽  
Ph Sensing ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence ◽  
Printed Patterns

Triazolopyridine–thiophene fluorophores exhibit high fluorescence quantum yields both in solution (80–89%) and in the solid state (13–26%). Because of an excellent and reversible pH induced fluorescence quenching/recovery, sensing devices such as fluorescent papers and complex inkjet-printed patterns are successfully fabricated for the detection of volatile acids both in solution and in a vapor atmosphere.

scholarly journals Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

2019 ◽  
Vol 15 ◽  
pp. 2684-2703 ◽  
Author(s):  
Natascha Breuer ◽  
Irina Gruber ◽  
Christoph Janiak ◽  
Thomas J J Müller
Keyword(s):  
Solid State ◽  
Michael Addition ◽  
Photophysical Properties ◽  
Ethyl Cyanoacetate ◽  
Product Formation ◽  
Quantum Yields ◽  
Substitution Pattern ◽  
Fluorescence Quantum Yields ◽  
Emission Enhancement ◽  
Donor Acceptor

Starting from substituted alkynones, α-pyrones and/or 1H-pyridines were generated in a Michael addition–cyclocondensation with ethyl cyanoacetate. The peculiar product formation depends on the reaction conditions as well as on the electronic substitution pattern of the alkynone. While electron-donating groups furnish α-pyrones as main products, electron-withdrawing groups predominantly give the corresponding 1H-pyridines. Both heterocycle classes fluoresce in solution and in the solid state. In particular, dimethylamino-substituted α-pyrones, as donor–acceptor systems, display remarkable photophysical properties, such as strongly red-shifted absorption and emission maxima with daylight fluorescence and fluorescence quantum yields up to 99% in solution and around 11% in the solid state, as well as pronounced emission solvatochromism. Also a donor-substituted α-pyrone shows pronounced aggregation-induced emission enhancement.

Structure Property Analysis of the Solution and Solid-State Properties of Bistable Photochromic Hydrazones

2019 ◽  
Author(s):  
Baihao Shao ◽  
Hai Qian ◽  
Quan Li ◽  
ivan aprahamian
Keyword(s):  
Solid State ◽  
Phenyl Group ◽  
Quantum Yields ◽  
Structure Property ◽  
Pull System ◽  
X Ray Crystallography ◽  
Fluorescence Quantum Yields ◽  
Property Analysis ◽  
Fluorescence Characteristics ◽  
Almost All

The development of new photochromic compounds, and the optimization of their photophysical and switching properties are prerequisites for accessing new functions and opportunities that are not possible with currently available systems. To this end we recently developed a new bistable hydrazone switch that undergoes efficient photoswitching and emission ON/OFF toggling in both solution and solid-state. Here, we present a systematic structure-property analysis using a family of hydrazones, and show how their properties, including activation wavelengths, photostationary states (PSSs), photoisomerization quantum yields, thermal half-lives (<i>t</i><sub>1/2</sub>), and solution/solid-state fluorescence characteristics vary as a function of electron donating (EDG) and/or withdrawing (EWG) substituents. These studies resulted in the red-shifting of the absorption profiles of the <i>Z</i> and <i>E</i> isomers of the switches, while maintaining excellent PSSs in almost all of the compounds. The introduction of <i>para</i>-NMe<sub>2</sub>, and/or <i>para</i>-NO<sub>2</sub> groups improved the photoisomerization quantum yields, and the extremely long thermal half-lives (tens to thousands of years) were maintained in most cases, even in a push-pull system, which can be activated solely with visible light. Hydrazones bearing EDGs at the stator phenyl group are an exception and show up to 6 orders of magnitude acceleration in<i>t</i><sub>1/2 </sub>(<i>i.e.</i>, days)<sub> </sub>because of a change in the isomerization mechanism. Moreover, we discovered that a <i>para</i>-NMe<sub>2</sub> group is required to have reasonable fluorescence quantum yields in solution, and that rigidification enhances the emission in the solid-state. Finally, X-ray crystallography analysis showed that the switching process is more efficient in the solid-state when the hydrazone is loosely packed.<br>

1,4,7,10-Tetraisoalkyltetracenes: Tuning of Solid-State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation (Eur. J. Org. Chem. 16/2010)

2010 ◽  
Vol 2010 (16) ◽  
pp. 2987-2987
Author(s):  
Chitoshi Kitamura ◽  
Hideki Tsukuda ◽  
Akio Yoneda ◽  
Takeshi Kawase ◽  
Takashi Kobayashi ◽  
...  
Keyword(s):  
Optical Properties ◽  
Solid State ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields

scholarly journals Emission Quenching in Tetraphenylfuran Crystal: Why This Propeller-Shaped Molecule Does Not Emit in the Condensed Phase?

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 522
Author(s):  
Ljiljana Stojanović ◽  
Rachel Crespo-Otero
Keyword(s):  
Solid State ◽  
Ground State ◽  
Light Emission ◽  
Quantum Yields ◽  
Triplet States ◽  
Fluorescence Quantum Yields ◽  
The Family ◽  
Emission Quenching ◽  
Significant Attention

Due to their substantial fluorescence quantum yields in the crystalline phase, propeller-shaped molecules have recently gained significant attention as potential emissive materials for optoelectronic applications. For the family of cyclopentadiene derivatives, light-emission is highly dependent on the nature of heteroatomic substitutions. In this paper, we investigate excited state relaxation pathways in the tetraphenyl-furan molecule (TPF), which in contrast with other molecules in the family, shows emission quenching in the solid-state. For the singlet manifold, our calculations show nonradiative pathways associated with C-O elongation are blocked in both vacuum and the solid state. A fraction of the population can be transferred to the triplet manifold and, subsequently, to the ground state in both phases. This process is expected to be relatively slow due to the small spin-orbit couplings between the relevant singlet-triplet states. Emission quenching in crystalline TPF seems to be in line with more efficient exciton hopping rates. Our simulations help clarify the role of conical intersections, population of the triplet states and crystalline structure in the emissive response of propeller-shaped molecules.

scholarly journals Remarkable Increase of Fluorescence Quantum Efficiency by Cyano Substitution on an ESIPT Molecule 2-(2-Hydroxyphenyl)benzothiazole: A Highly Photoluminescent Liquid Crystal Dopant

Crystals ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1105
Author(s):  
Tsuneaki Sakurai ◽  
Masaya Kobayashi ◽  
Hiroyuki Yoshida ◽  
Masaki Shimizu
Keyword(s):  
Liquid Crystal ◽  
Excited State ◽  
Solid State ◽  
Room Temperature ◽  
Cyano Group ◽  
Stokes Shift ◽  
Phenyl Group ◽  
Intramolecular Proton Transfer ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields

Fluorescent molecules with excited-state intramolecular proton transfer (ESIPT) character allow the efficient solid-state luminescence with large Stokes shift that is important for various applications, such as organic electronics, photonics, and bio-imaging fields. However, the lower fluorescence quantum yields (ΦFL) in the solution or viscous media, due to their structural relaxations in the excited state to reach the S0/S1 conical intersection, shackle further applications of ESIPT-active luminophores. Here we report that the introduction of a cyano group (-CN) into the phenyl group of 2-(2-hydroxyphenyl)benzothiazole (HBT), a representative ESIPT compound, remarkably increase its fluorescence quantum yield (ΦFL) from 0.01 (without -CN) to 0.49 (with -CN) in CH2Cl2, without disturbing its high ΦFL (=0.52) in the solid state. The large increase of the solution-state ΦFL of the cyano-substituted HBT (CN-HBT) is remarkable, comparing with our previously reported ΦFL values of 0.05 (with 4-pentylphenyl), 0.07 (with 1-hexynyl), and 0.15 (with 4-pentylphenylethynyl). Of interest, the newly-synthesized compound, CN-HBT, is miscible in a conventional room-temperature nematic liquid crystal (LC), 4-pentyl-4′-cyano biphenyl (5CB), up to 1 wt% (~1 mol%), and exhibits a large ΦFL of 0.57 in the viscous LC medium. A similar ΦFL value of ΦFL = 0.53 was also recorded in another room-temperature LC, trans-4-(4-pentylcyclohexyl)benzonitrile (PCH5), with a doping ratio of 0.5 wt% (~0.5 mol%). These 5CB/CN-HBT and PCH5/CN-HBT mixtures serve as light-emitting room-temperature LCs, and show anisotropic fluorescence with the dichroic ratio of 3.1 upon polarized excitation, as well as electric field response of luminescence intensity changes.

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