scholarly journals A New Pathway for the Synthesis of a New Class of Blue Fluorescent Benzofuran Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1968 ◽  
Author(s):  
Costel Moldoveanu ◽  
Ionel Mangalagiu ◽  
Dragos Lucian Isac ◽  
Anton Airinei ◽  
Gheorghita Zbancioc
Keyword(s):  
Substantial Reduction ◽  
Fluorescence Emission ◽  
Single Type ◽  
Quantum Yields ◽  
Dependent Manner ◽  
Fluorescent Properties ◽  
New Class ◽  
Straightforward Method ◽  
Short Period ◽  
Mw Irradiation

In this study an efficient and straightforward method for obtaining a new class of blue fluorescent bezofuran derivatives, under microwave irradiation, as well as under conventional thermal heating, is presented. Under conventional TH the reactions occur selectively, and a single type of benzofuran ester derivative was obtained. The synthesis under MW irradiation also led to benzofuran derivatives, but in a time-dependent manner. Irradiation for a short period of time led to a mixture of two types of benzofuran derivatives (3a–c and 4a–c), while MW irradiation for a longer period of time led to a single type of benzofuran (3-methylbenzofuran), the reaction becoming highly selective. Taking into consideration the advantages offered by MW irradiation in terms of a substantial decrease of solvent consumed, a substantial reduction in reaction time (from days to hours), and a consequent diminution in energy consumption, these methods could be considered environmentally friendly. Here, feasible reaction mechanisms for the benzofuran derivatives formation are described. The absorption and fluorescence emission of the obtained benzofuran derivatives were studied, with part of these compounds being intense blue emitters. A certain influence of the benzofuran substituents concerning absorption and fluorescent properties was observed. Only compounds anchored with a carbomethoxy group of furan ring have shown good quantum yields.

scholarly journals Nature of Linear Spectral Properties and Fast Electronic Relaxations in Green Fluorescent Pyrrolo[3,4-c]Pyridine Derivative

2021 ◽  
Vol 22 (11) ◽  
pp. 5592
Author(s):  
Nataliia V. Bashmakova ◽  
Yevgeniy O. Shaydyuk ◽  
Andriy M. Dmytruk ◽  
Tomasz Świergosz ◽  
Olexiy D. Kachkovsky ◽  
...  
Keyword(s):  
Steady State ◽  
Transient Absorption ◽  
Stokes Shift ◽  
Fluorescence Emission ◽  
Quantum Yields ◽  
Pyridine Derivative ◽  
Relaxation Processes ◽  
Spectroscopic Techniques ◽  
Fluorescent Properties ◽  
Light Amplification

The electronic nature of 4-hydroxy-1H-pyrrolo[3,4-c]pyridine-1,3,6(2H,5H)-trione (HPPT) was comprehensively investigated in liquid media at room temperature using steady-state and time-resolved femtosecond transient absorption spectroscopic techniques. The analysis of the linear photophysical and photochemical parameters of HPPT, including steady-state absorption, fluorescence and excitation anisotropy spectra, along with the lifetimes of fluorescence emission and photodecomposition quantum yields, revealed the nature of its large Stokes shift, specific changes in the permanent dipole moments under electronic excitation, weak dipole transitions with partially anisotropic character, and high photostability. Transient absorption spectra of HPPT were obtained with femtosecond resolution and no characteristic solvate relaxation processes in protic (methanol) solvent were revealed. Efficient light amplification (gain) was observed in the fluorescence spectral range of HPPT, but no super-luminescence and lasing phenomena were detected. The electronic structure of HPPT was also analyzed with quantum-chemical calculations using a DFT/B3LYP method and good agreement with experimental data was shown. The development and investigation of new pyrrolo[3,4-c]pyridine derivatives are important due to their promising fluorescent properties and potential for use in physiological applications.

Symmetry Breaking and the Turn-On Fluorescence of Small, Highly Strained Carbon Nanohoops

2019 ◽  
Author(s):  
Terri Lovell ◽  
Curtis Colwell ◽  
Lev N. Zakharov ◽  
Ramesh Jasti
Keyword(s):  
Symmetry Breaking ◽  
Theoretical Work ◽  
P Systems ◽  
Quantum Yields ◽  
Size Dependent ◽  
New Class ◽  
Carbon Carbon Bond ◽  
Conjugated Macrocycles ◽  
Structural Manipulation ◽  
Highly Strained

<p>[<i>n</i>]Cycloparaphenylenes, or “carbon nanohoops,” are unique conjugated macrocycles with radially oriented p-systems similar to those in carbon nanotubes. The centrosymmetric nature and conformational rigidity of these molecules lead to unusual size-dependent photophysical characteristics. To investigate these effects further and expand the family of possible structures, a new class of related carbon nanohoops with broken symmetry is disclosed. In these structures, referred to as <i>meta</i>[<i>n</i>]cycloparaphenylenes, a single carbon-carbon bond is shifted by one position in order to break the centrosymmetric nature of the parent [<i>n</i>]cycloparaphenylenes. Advantageously, the symmetry breaking leads to bright emission in the smaller nanohoops, which are typically non-fluorescent due to optical selection rules. Moreover, this simple structural manipulation retains one of the most unique features of the nanohoop structures-size dependent emissive properties with relatively large extinction coefficents and quantum yields. Inspired by earlier theoretical work by Tretiak and co-workers, this joint synthetic, photophysical, and theoretical study provides further design principles to manipulate the optical properties of this growing class of molecules with radially oriented p-systems.</p>

Symmetry Breaking and the Turn-On Fluorescence of Small, Highly Strained Carbon Nanohoops

2019 ◽  
Author(s):  
Terri Lovell ◽  
Curtis Colwell ◽  
Lev N. Zakharov ◽  
Ramesh Jasti
Keyword(s):  
Symmetry Breaking ◽  
Theoretical Work ◽  
P Systems ◽  
Quantum Yields ◽  
Size Dependent ◽  
New Class ◽  
Carbon Carbon Bond ◽  
Conjugated Macrocycles ◽  
Structural Manipulation ◽  
Highly Strained

<p>[<i>n</i>]Cycloparaphenylenes, or “carbon nanohoops,” are unique conjugated macrocycles with radially oriented p-systems similar to those in carbon nanotubes. The centrosymmetric nature and conformational rigidity of these molecules lead to unusual size-dependent photophysical characteristics. To investigate these effects further and expand the family of possible structures, a new class of related carbon nanohoops with broken symmetry is disclosed. In these structures, referred to as <i>meta</i>[<i>n</i>]cycloparaphenylenes, a single carbon-carbon bond is shifted by one position in order to break the centrosymmetric nature of the parent [<i>n</i>]cycloparaphenylenes. Advantageously, the symmetry breaking leads to bright emission in the smaller nanohoops, which are typically non-fluorescent due to optical selection rules. Moreover, this simple structural manipulation retains one of the most unique features of the nanohoop structures-size dependent emissive properties with relatively large extinction coefficents and quantum yields. Inspired by earlier theoretical work by Tretiak and co-workers, this joint synthetic, photophysical, and theoretical study provides further design principles to manipulate the optical properties of this growing class of molecules with radially oriented p-systems.</p>

A (4,4)-connected zinc(II) coordination polymer constructed with the flexible 2-carboxy phenoxyacetate ligand: synthesis, conformation alteration and fluorescent properties

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Jun-Xia Li ◽  
Tian Zhang ◽  
He-Jun Chen ◽  
Zhong-Xiang Du
Keyword(s):  
Coordination Polymer ◽  
Hydrothermal Reaction ◽  
Layer Structure ◽  
Fluorescence Emission ◽  
Phenoxyacetic Acid ◽  
X Ray Diffraction ◽  
Fluorescent Properties ◽  
Sulfate Heptahydrate ◽  
X Ray ◽  
Related Compounds

Abstract A new binary ZnII coordination polymer, [Zn(2-cpa)(H2O)] n (2D-Zn) has been prepared by a 120 °C hydrothermal reaction of zinc(II) sulfate heptahydrate and 2-carboxy phenoxyacetic acid (2-H2cpa) in the presence of potassium hydroxide. Single-crystal X-ray diffraction analysis shows that the ZnII ion is located in a deformed ZnO6 octahedron bonded by one water and three 2-carboxy phenoxyacetate (2-cpa) ligands. The 2-cpa exhibits pentadentate double bridging chelate-μ 3 coordination mode and connects adjacent ZnII ions to generate a corrugated (4,4)-connected layer structure. The structures, conformation of 2-cpa and photoluminescence spectra for 2D-Zn have been carefully analyzed and compared with its two closely related compounds ̶ 1D [Zn(2-cpa)(H2O)] n (1D-Zn) and mononuclear [Zn(2-cpa)(H2O)3] (0D-Zn). The results showed that the conformation of 2-cpa in 2D-Zn has the maximum alteration and the corresponding fluorescence emission peak of 2D-Zn has the largest red-shift of 62 nm compared with that of free 2-H2cpa.

scholarly journals Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

2019 ◽  
Vol 15 ◽  
pp. 474-489 ◽  
Author(s):  
Andrejs Šišuļins ◽  
Jonas Bucevičius ◽  
Yu-Ting Tseng ◽  
Irina Novosjolova ◽  
Kaspars Traskovskis ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Secondary Amines ◽  
Acetonitrile Solution ◽  
Quantum Yields ◽  
Cell Labelling ◽  
Aromatic Substitution ◽  
Fluorescent Properties ◽  
Substitution Reactions ◽  
Low Cytotoxicity ◽  
Electron Donating Groups

The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future.

scholarly journals Luminescent Hybrid Materials Based on Curcumin Derivatives Embedded in Palygorskite

2018 ◽  
Vol 55 (1) ◽  
pp. 63-67
Author(s):  
Monica Florentina Raduly ◽  
Valentin Raditoiu ◽  
Alina Raditoiu ◽  
Luminita Eugenia Wagner ◽  
Viorica Amariutei ◽  
...  
Keyword(s):  
Hybrid Materials ◽  
Fluorescence Spectra ◽  
Fluorescence Emission ◽  
Emission Spectra ◽  
Hydroxyl Groups ◽  
Fluorescent Properties ◽  
Fluorescence Emission Spectra ◽  
Curcumin Derivatives ◽  
Absorption Studies ◽  
Inorganic Matrix

The seven curcumin derivatives were deposited on palygorskite in order to obtain hybrid materials. The fluorescence emission spectra of the obtained materials show a decrease in fluorescence intensity relative to the respective dyes, due to the environments around the dyestuff molecules created in the host matrices. Absorption studies show the best adsorption on the inorganic matrix, for the compounds with the hydroxyl groups. Correlating fluorescence spectra of hybrid materials with the results for absorption spectra of the dyes adsorbtion on the surface of the clay lead to the conclusion that a high percentage of the adsorbed dye had the effect of fluorescence quenching. Thus, it was confirmed that the fluorescent properties of hybrid materials depend on the interactions established between the fluorescent dyestuff and the inorganic network.

scholarly journals Dansylated analogues of the opioid peptide [Dmt1]DALDA: in vitro activity profiles and fluorescence parameters.

2004 ◽  
Vol 51 (1) ◽  
pp. 107-113 ◽  
Author(s):  
Irena Berezowska ◽  
Carole Lemieux ◽  
Nga N Chung ◽  
Bogumil Zelent ◽  
Peter W Schiller
Keyword(s):  
Hydrophobic Interactions ◽  
Fluorescence Emission ◽  
Opioid Peptide ◽  
Quantum Yields ◽  
Binding Studies ◽  
Dansyl Group ◽  
Distribution Studies ◽  
Peptide Agonist ◽  
Diaminopropionic Acid

Dansylated analogues of the potent and selective micro opioid peptide agonist [Dmt(1)]DALDA (H-Dmt-D-Arg-Phe-Lys-NH(2); Dmt = 2',6'-dimethyltyrosine) were prepared either by substitution of N(beta)-dansyl-alpha,beta-diaminopropionic acid or N(epsilon)-dansyllysine for Lys(4), or by attachment of a dansyl group to the C-terminal carboxamide function via a linker. All three analogues displayed high micro agonist potency in vitro and the C-terminally dansylated one retained significant micro receptor selectivity. The three analogues showed interesting differences in their fluorescence emission maxima and quantum yields, indicating that the dansyl group in two of them was engaged in intramolecular hydrophobic interactions. These dansylated [Dmt(1)]DALDA analogues represent valuable tools for binding studies, cellular uptake and intracellular distribution studies, and tissue distribution studies.

scholarly journals Rhythmic Accessibility to Sequential Working Memory in a Theta Phase-Dependent Manner

2021 ◽  
Author(s):  
Takuya Ideriha ◽  
Junichi Ushiyama
Keyword(s):  
Working Memory ◽  
Memory Storage ◽  
Dependent Manner ◽  
Random Interval ◽  
Phase Coding ◽  
Short Period ◽  
Theta Phase ◽  
Sequential Information ◽  
The Impact ◽  
Theta Range

Working memory is active short-term memory storage that is easily accessible and underlies various activities, such as maintaining phone numbers in mind for a short period [1,2]. There is accumulating theoretical and physiological evidence that memorized items are represented rhythmically by neural oscillation in the theta range (4-7 Hz) [3,4]. However, the impact of this process on human behavior is yet to be examined. Here we show that simply memorizing sequential information affects a behavioral index (i.e., reaction time, RT) in a rhythmic manner. In the main experiment (Experiment 1), we measured RTs to a visual probe that appeared at one of two sequentially memorized locations after a random interval. Consequently, RTs to the first and second probes each fluctuated in the theta range as a function of the random interval, and the phases of the two theta fluctuations were not in phase or anti-phase, but shifted by approximately 270 degree. Interestingly, the 270 degree phase difference corresponded to the rhythm of "phase coding", where sequential information is represented on the specific phase of theta oscillation [5-7]. These relationships were not observed in tasks simply requiring attention (Experiment 2) or memorization (Experiment 3) of spatial locations without sequential order. In conclusion, the current results demonstrate that our behavior fluctuates when recalling memorized sequential items in the theta-range, suggesting that accessibility to sequential working memory is rhythmic rather than stable, possibly reflecting theta-phase coding.

Study on Photochromic Materials with a Novel Photochromic Diarylethene use for Polarization Holographic Recording

2013 ◽  
Vol 763 ◽  
pp. 61-64 ◽  
Author(s):  
Shang Hua He ◽  
Gang Liu ◽  
Shi Qiang Cui
Keyword(s):  
Fluorescence Spectra ◽  
Uv Light ◽  
Amorphous Film ◽  
Quantum Yields ◽  
Holographic Recording ◽  
Pmma Film ◽  
Recording Medium ◽  
Fluorescent Properties ◽  
Image Recording ◽  
Photochromic Materials

A novel unsymmetrical photochromic diarylethene 1-(2, 5-dimethyl-3-thienyl)-2-[2-methyl-5-(2,2-dibutylfluorene)-3-thienyperfluorocyclo-pentene (1o) was synthesized and its photochromic and fluorescent properties were investigated. Diarylethene 1 changed the color from colorless to hyacinthine upon irradiation with 297 nm UV light, in which absorption maxima were observed at 554 nm in hexane and at 565 nm in PMMA amorphous film, respectively. This new photochromic system also exhibited remarkable fluorescence intensity both in solution and in PMMA film. The fluorescence spectra showed a systematic red-shift with the emission intensity of diarylethene 1 in a photo-stationary state was quenched to ca. 64%. The cyclization and cycloreversion quantum yields of 1 in hexane were determined to be 0.56 and 0.002. Polarization multiplexed image recording can be carried out in this diarylethene 1c/PMMA film as recording medium film.

Oscillatory flow regimes around four cylinders in a diamond arrangement

2019 ◽  
Vol 877 ◽  
pp. 955-1006 ◽  
Author(s):  
Chengjiao Ren ◽  
Liang Cheng ◽  
Feifei Tong ◽  
Chengwang Xiong ◽  
Tingguo Chen
Keyword(s):  
Oscillatory Flow ◽  
Bluff Body ◽  
Substantial Reduction ◽  
Period Doubling ◽  
Flow Regimes ◽  
Mode Competition ◽  
Single Type ◽  
Phase Dynamics ◽  
Flow Features ◽  
Four Cylinders

Oscillatory flow around a cluster of four circular cylinders in a diamond arrangement is investigated using two-dimensional direct numerical simulation over Keulegan–Carpenter numbers (KC) ranging from 4 to 12 and Reynolds numbers (Re) from 40 to 230 at four gap-to-diameter ratios (G) of 0.5, 1, 2 and 4. Three types of flows, namely synchronous, quasi-periodic and desynchronized flows (along with 14 flow regimes) are mapped out in the (G, KC, Re)-parameter space. The observed flow characteristics around four cylinders in a diamond arrangement show a few unique features that are absent in the flow around four cylinders in a square arrangement reported by Tong et al. (J. Fluid Mech., vol. 769, 2015, pp. 298–336). These include (i) the dominance of flow around the cluster-scale structure at $G=0.5$ and 1, (ii) a substantial reduction of regime D flows in the regime maps, (iii) new quasi-periodic (phase trapping) $\text{D}^{\prime }$ (at $G=0.5$ and 1) and period-doubling $\text{A}^{\prime }$ flows (at $G=1$) and most noteworthily (iv) abnormal behaviours at ($G\leqslant 2$) (referred to as holes hereafter) such as the appearance of spatio-temporal synchronized flows in an area surrounded by a single type of synchronized flow in the regime map ($G=0.5$). The mode competition between the cluster-scale and cylinder-scale flows is identified as the key flow mechanism responsible for those unique flow features, with the support of evidence derived from quantitative analysis. Phase dynamics is introduced for the first time in bluff-body flows, to the best knowledge of the authors, to quantitatively interpret the flow response (e.g. quasi-periodic flow features) around the cluster. It is instrumental in revealing the nature of regime $\text{D}^{\prime }$ flows where the cluster-scale flow features are largely synchronized with the forcing of incoming oscillatory flow (phase trapping) but are modulated by localized flow features.

Sign in / Sign up

Export Citation Format

Share Document