Synthesis and photophysical properties of benzo[c]phenanthrene derivatives

Background: Three polycyclic aromatic hydrocarbons derived from benzo[c]phenanthrene have been synthesized through a one-step procedure involving palladium Suzuki coupling and are characterized by 1 H and 13C NMR, MS and HRMS spectroscopies. Methods: UV-vis absorption and fluorescence properties of these π-conjugated compounds have been evaluated in solutions and strong emission in the blue region of the visible spectrum was noted. Results: The optical spectra of these small polycyclic aromatic compounds are unusual because absorption is entirely in the UV region (λmax = 281-285 nm), yet fluorescence occurs at 410-422 nm. Conclusion: This equates to a Stokes shift of 1.32-1.39 eV (10756-11256 cm−1 ) and is among the large Stokes shifts that have been reported for small molecules, making them promising candidates for optoelectronic applications.

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One-Step Synthesis of Indolizino[3,4,5-ab]isoindoles by Manganese(I)-Catalyzed C–H Activation: Structural Studies and Photophysical Properties

Organic & Biomolecular Chemistry ◽

10.1039/d1ob02246f ◽

2022 ◽

Author(s):

Sara Cembellin ◽

Ivan Maisuls ◽

Constantin Gabriel Daniliuc ◽

Helena Osthues ◽

Nikos Doltsinis ◽

...

Keyword(s):

Photophysical Properties ◽

Regioselective Synthesis ◽

Luminescence Properties ◽

Structural Studies ◽

Step Procedure ◽

One Step

Herein, a regioselective synthesis of indolizino[3,4,5-ab]isoindoles (INIs), a valuable class of heterocycles with interesting luminescence properties, is described using manganese(I)-catalyzed C−H activation. The reported transformation proceeds in a one-step procedure...

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Counter Anion Effect on the Photophysical Properties of Emissive Indolizine-Cyanine Dyes in Solution and Solid State

Molecules ◽

10.3390/molecules23123051 ◽

2018 ◽

Vol 23 (12) ◽

pp. 3051 ◽

Cited By ~ 9

Author(s):

Jacqueline Gayton ◽

Shane Autry ◽

Ryan Fortenberry ◽

Nathan Hammer ◽

Jared Delcamp

Keyword(s):

Thin Films ◽

Solid State ◽

Near Infrared ◽

Photophysical Properties ◽

Stokes Shift ◽

Counter Anion ◽

Anion Effect ◽

Research Areas ◽

Active Research ◽

Stokes Shifts

Near-infrared emissive materials with tunable Stokes shifts and solid-state emissions are needed for several active research areas and applications. To aid in addressing this need, a series of indolizine-cyanine compounds varying only the anions based on size, dipole, and hydrophilicity were prepared. The effect of the non-covalently bound anions on the absorption and emission properties of identical π-system indolizine-cyanine compounds were measured in solution and as thin films. Interestingly, the anion choice has a significant influence on the Stokes shift and molar absorptivities of the dyes in solution. In the solid-state, the anion choice was found to have an effect on the formation of aggregate states with higher energy absorptions than the parent monomer compound. The dyes were found to be emissive in the NIR region, with emissions peaking at near 900 nm for specific solvent and anion selections.

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Synthesis and characterization of pine-cone derived carbon-based solid acid: a green and recoverable catalyst for the synthesis of pyrano_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazolidinedione derivatives

Letters in Organic Chemistry ◽

10.2174/1570178617666200210105635 ◽

2020 ◽

Vol 17 ◽

Author(s):

Fatemeh Ghorbani ◽

Seied Ali Pourmousavi ◽

Hamzeh Kiyani

Keyword(s):

Simple Procedure ◽

Reaction Times ◽

Pine Cone ◽

Step Procedure ◽

Recoverable Catalyst ◽

Nano Catalyst ◽

Polycyclic Aromatic ◽

One Step ◽

Amidoalkyl Naphthol ◽

Carbon Based

: In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180 ˚C in a sealed autoclave in one-step procedure. The resulted Nano catalyst was characterized by FT-IR, TGA, XRD, FE-SEM and elemental analysis (EA). The result of characterization was shown that the carbon-based acid is amorphous with polycyclic aromatic carbon sheets attached plentiful -OH, -COOH, and -SO3H groups. The catalytic activities of Pine-SO3H was investigated in the highly efficient synthesis of pyrano[2,3-c] pyrazole, amino-benzochromenes, amidoalkyl naphthol and 5-arylidene-2,4-thiazolidinedione derivatives. The application of Pine-SO3H in the synthesis, offers several advantages such as simple procedure with an easy work-up, recoverable catalyst, mild condition, eco-friendliness, excellent yields, short reaction times and use of an inexpensive catalyst.

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Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Chemosensors ◽

10.3390/chemosensors10010019 ◽

2022 ◽

Vol 10 (1) ◽

pp. 19

Author(s):

Abigail E. Reese ◽

Charles Lochenie ◽

Ailsa Geddis ◽

Luana A. Machado ◽

Marcos C. de Souza ◽

...

Keyword(s):

Immune Cells ◽

Emission Spectroscopy ◽

Rational Design ◽

Cell Imaging ◽

Photophysical Properties ◽

Stokes Shift ◽

Design And Synthesis ◽

Confocal Fluorescence ◽

Absorption And Emission Spectroscopy ◽

Stokes Shifts

Five new disubstituted 2,6-thioaryl-BODIPY dyes were synthesized via selective aromatic electrophilic substitution from commercially available thiophenols. The analysis of the photophysical properties via absorption and emission spectroscopy showed unusually large Stokes shifts for BODIPY fluorophores (70–100 nm), which makes them suitable probes for bioimaging. Selected compounds were evaluated for labelling primary immune cells as well as different cancer cell lines using confocal fluorescence microscopy.

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Intriguing Heteroleptic ZnII bis(dipyrrinato) Emitters in the Far-Red Region With Large Pseudo-Stokes Shift for Bioimaging

Frontiers in Chemistry ◽

10.3389/fchem.2021.754420 ◽

2021 ◽

Vol 9 ◽

Author(s):

Roberta Tabone ◽

Dominik Feser ◽

Enrico D. Lemma ◽

Ute Schepers ◽

Claudia Bizzarri

Keyword(s):

Cell Imaging ◽

Photophysical Properties ◽

Stokes Shift ◽

Nonradiative Transition ◽

Excitation Spectra ◽

Polar Solvents ◽

Heteroleptic Complexes ◽

Intense Emission ◽

Characteristic Features ◽

Stokes Shifts

Novel heteroleptic ZnII bis(dipyrrinato) complexes were prepared as intriguing emitters. With our tailor-made design, we achieved far-red emissive complexes with a photoluminescence quantum yield up to 45% in dimethylsulfoxide and 70% in toluene. This means that heteroleptic ZnII bis(dipyrrinato) complexes retain very intense emission also in polar solvents, in contrast to their homoleptic counterparts, which we prepared for comparing the photophysical properties. It is evident from the absorption and excitation spectra that heteroleptic complexes present the characteristic features of both ligands: the plain dipyrrin (Lp) and the π-extended dipyrrin (Lπ). On the contrary, the emission comes exclusively from the π-extended dipyrrin Lπ, suggesting an interligand nonradiative transition that causes a large pseudo-Stokes shift (up to 4,600 cm−1). The large pseudo-Stokes shifts and the emissive spectral region of these novel heteroleptic ZnII bis(dipyrrinato) complexes are of great interest for bioimaging applications. Thus, their high biocompatibiliy with four different cell lines make them appealing as new fluorophores for cell imaging.

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A quick one-step synthesis of luminescent gold nanospheres

Soft Matter ◽

10.1039/d0sm02024a ◽

2020 ◽

Vol 16 (48) ◽

pp. 10865-10868

Author(s):

Angela Candreva ◽

Giuseppe Di Maio ◽

Massimo La Deda

Keyword(s):

Visible Spectrum ◽

Luminescence Properties ◽

Gold Nanospheres ◽

Step Procedure ◽

Wide Range ◽

One Step ◽

Application Fields

Luminescent gold nanospheres emissive in a wide range of the visible spectrum have been synthesized by a quick one-step procedure; the coexistence of the plasmonic and luminescence properties makes them useful in various application fields.

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Dibenzochrysene Enables Tightly Controlled Docking and Stabilizes Photoexcited States in Dual-Pore Covalent Organic Frameworks

10.26434/chemrxiv.9638633.v1 ◽

2019 ◽

Author(s):

Torben Sick ◽

Niklas Keller ◽

Nicolai Bach ◽

Andreas Koszalkowski ◽

Julian Rotter ◽

...

Keyword(s):

Molecular Docking ◽

Photophysical Properties ◽

Visible Spectrum ◽

Large Family ◽

Building Blocks ◽

Band Gaps ◽

Docking Site ◽

Covalent Organic Frameworks ◽

Connected Node ◽

Optoelectronic Applications

Covalent organic frameworks (COFs), consisting of covalently connected organic building units, combine attractive features such as crystallinity, open porosity and widely tunable physical properties. For optoelectronic applications, the incorporation of heteroatoms into a 2D COF has the potential to yield desired photophysical properties such as lower band gaps, but can also cause lateral offsets of adjacent layers. Here, we introduce dibenzo[g,p]chrysene (DBC) as a novel building block for the synthesis of highly crystalline and porous 2D dual-pore COFs showing interesting properties for optoelectronic applications. The newly synthesized terephthalaldehyde (TA), biphenyl (Biph), and thienothiophene (TT) DBC-COFs combine conjugation in the a,b-plane with a tight packing of adjacent layers guided through the molecular DBC node serving a specific docking site for successive layers. The resulting DBC-COFs exhibit a hexagonal dual-pore kagome geometry, which is comparable to COFs containing another molecular docking site, namely 4,4′,4″,4‴-(ethylene-1,1,2,2-tetrayl)-tetraaniline (ETTA). In this context, the respective interlayer distances decrease from about 4.60 Å in ETTA-COFs to about 3.6 Å in DBC-COFs, leading to well-defined hexagonally faceted single crystals sized about 50-100 nm. The TT DBC-COFs feature broad light absorption covering large parts of the visible spectrum, while Biph DBC-COF shows extraordinary excited state lifetimes exceeding 10 ns. In combination with the large number of recently developed linear conjugated building blocks, the new DBC tetra-connected node is expected to enable the synthesis of a large family of strongly p-stacked, highly ordered 2D COFs with promising optoelectronic properties.

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Electrochromic Performance and Capacitor Performance of α-MoO3 Nanorods Fabricated by a One-Step Procedure

Coatings ◽

10.3390/coatings11070783 ◽

2021 ◽

Vol 11 (7) ◽

pp. 783

Author(s):

Ying Duan ◽

Chen Wang ◽

Jian Hao ◽

Yang Jiao ◽

Yanchao Xu ◽

...

Keyword(s):

Growth Parameters ◽

Average Diameter ◽

Fast Response ◽

Cycle Stability ◽

Electrochromic Devices ◽

Step Procedure ◽

One Step ◽

Supercapacitor Performance ◽

First Time ◽

Prepared Nanorods

In this paper, we propose for the first time the synthesis of α-MoO3 nanorods in a one-step procedure at mild temperatures. By changing the growth parameters, the microstructure and controllable morphology of the resulting products can be customized. The average diameter of the as-prepared nanorods is about 200 nm. The electrochromic and capacitance properties of the synthesized products were studied. The results show that the electrochromic properties of α-MoO3 nanorods at 550 nm have 67% high transmission contrast, good cycle stability and fast response time. The MoO3 nanorods also exhibit a stable supercapacitor performance with 98.5% capacitance retention after 10,000 cycles. Although current density varies sequentially, the nanostructure always exhibits a stable capacitor to maintain 100%. These results indicate the as-prepared MoO3 nanorods may be good candidates for applications in electrochromic devices and supercapacitors.

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Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes

Chemosensors ◽

10.3390/chemosensors9010016 ◽

2021 ◽

Vol 9 (1) ◽

pp. 16

Author(s):

Yingchun Wang ◽

Tomas Opsomer ◽

Wim Dehaen

Keyword(s):

Stokes Shift ◽

Substituent Effects ◽

Visible Spectrum ◽

Fluorescent Sensors ◽

Biological Imaging ◽

Fluorescent Imaging ◽

Fluorescence Properties ◽

Imaging Probes ◽

Synthetic Methodologies ◽

Aromatic Heterocyclic

The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed.

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