Fluorescent cyclopentadithiophene derivatives having phenyl-substituted silyl moieties

Hanamura, Hitoshi; Haneishi, Ryoko; Nemoto, Nobukatsu

doi:10.1016/j.tetlet.2011.05.128

Cited by 8 publications

(4 citation statements)

References 28 publications

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“…The hypsochromic shift is attributed to a reduction of the effective conjugation length due to self‐association occurring because of a relatively weak hydrogen bond between the o ‐hydroxy group and the imine bridge . In the literature, the hyperchromic effects are based on an increase in the dipole moments of the HOMO and LUMO states owing to the σ–π conjugation in the HOMO and the σ *– π * conjugation in the LUMO . Very few polymer types so far have presented such properties .…”

Section: Resultsmentioning

confidence: 99%

“…40 -42 In the literature, the hyperchromic effects are based on an increase in the dipole moments of the HOMO and LUMO states owing to the -conjugation in the HOMO and the *-* conjugation in the LUMO. 43 Very few polymer types so far have presented such properties. 44 -46 Some compounds, like cis-trans polyarenes and denaturation of the DNA molecule as well as some thiophene derivatives, have been shown to have both bathochromic and hyperchromic effects.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis route to regioselectively functionalized bifunctional polyarene

2015

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We report the regioselective oxidative synthesis of polyaminonaphthol sulfonic acid (PANSA) particles and firstly obtained nanoparticles with molecular weight of ca 23 200 g mol−1 using a template‐free polymerization process in which NaOCl was used as an oxidant in aqueous basic medium. Nanoparticles were characterized using NMR, Fourier transform infrared and UV‐visible spectroscopies, gel permeation chromatography, thermogravimetry (TG), differential scanning calorimetry (DSC), cyclic voltammetry, photoluminescence (PL), dynamic light scattering, X‐ray diffraction, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and conductivity techniques. SEM and TEM analyses showed that the nanoparticles had a self‐stabilizing structure interconnecting with micro‐channels. PANSA also exhibited reversible redox behaviour due to its electroactive nature. Nanoparticles display a slight hypsochromic shift and hyperchromic effect with higher intensity in PL spectra and also emitted an intense white light in dimethylsulfoxide. In addition, the thermal stability of PANSA was investigated using TG and DSC techniques. Finally, the kinetic parameters related to the solid‐state thermal decomposition of PANSA were calculated from non‐isothermal methods based on multiple heating rates. © 2015 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis route to regioselectively functionalized bifunctional polyarene

2015

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“…[5] On the other hand, the red-shifts of the wavelength in the absorption as well as emission spectra and the improvement of the fluorescence quantum yields have been reported by introducing alkylsilyl groups onto the aromatic ring. [6][7][8][9] Our research group has also reported that poly(tetramethylsilarylenesiloxane) derivatives where the aromatic moiety is introduced into the main chain component of polysiloxane improve the heat resistance and fluorescence quantum yield. [10][11][12][13][14][15] Based on the above background, we synthesized dibenzothiophene derivatives with trimethylsilyl groups as well as poly(tetramethylsilarylenesiloxane) derivatives bearing dibenzothiophene moiety as shown in Scheme 1 in this research.…”

Section: Introductionmentioning

confidence: 99%

Thermal and Optical Properties of Dibenzothiophene-Based Poly(tetramethylsilarylenesiloxane) Derivatives

Okura

Katoh

Ichikawa

et al. 2020

Trans. Mat. Res. Soc. Japan

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The synthesis of dibenzothiophene derivative, i.e., 2,8-bis(trimethylsilyl)dibenzothiophene (3a) and dibenzothiophene-based poly(tetramethylsilarylenesiloxane) derivative (P1) was attained. In addition, 2,8-bis(trimethylsilyl)dibenzothiophene-5,5'-dioxide (3aO) and oxidized dibenzothiophene-based poly(tetramethylsilarylenesiloxane) derivative (P1O) were obtained by oxidation reaction of 3a and P1, respectively. The glass transition temperature was raised by the oxidation of the dibenzothiophene-based poly(tetramethylsilarylenesiloxane) derivative. The introduction of alkylsilyl groups onto dibenzothiophene derivatives induced no remarkable red shifts in the absorption as well as fluorescence spectra; however, the red shifts in the fluorescence spectra were observed by oxidation of dibenzothiophene derivatives.

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“…There has been a considerable interest to the synthesis and investigation of branched, starshaped and dendritic silicon-containing oligothiophenes since a discovery of the phenomenon of increased luminescence efficiency as compared to their linear analogs [22][23][24][25]. Moreover, organosilicon derivatives of various luminophores attract much attention of researchers due to their interesting optical properties [26][27][28]. The absence of π-conjugation through silicon atom between the adjacent luminophores in this type of molecules allows re-alizing the efficient intramolecular inductive-resonance transfer of the electronic excitation energy from the outer luminophores (donors) with a wider band gap to the inner luminophore (acceptor) with a lower band gap [29].…”

Section: Introductionmentioning

confidence: 99%

Nanostructured Organosilicon Luminophores for Effective Light Conversion in Organic Light Emitting Diodes

Luponosov¹,

Сурин²,

Susarova³

et al. 2015

Organic Photonics and Photovoltaics

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Full characterization of nanostructured organosilicon luminophores NOL4 and NOL5 based on the donor 2,2'-bithiophene and acceptor 1,4-bis(2,2 ′ -bithiophene-5-yl)benzene units in dilute solutions and thin films by UV-Vis spectroscopy, DSC, TGA and X-ray techniques was reported. It was found that usage of these molecules as dopants (10-20 wt%) to the electroactive polyfluorene host in organic light-emitting devices (OLEDs) leads to the efficient spectral long wavelength shifting of the electroluminescence and an increase of the OLED performance as compared to the devices based on pristine polyfluorene, NOL4 and NOL5.

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Fluorescent cyclopentadithiophene derivatives having phenyl-substituted silyl moieties

Cited by 8 publications

References 28 publications

Synthesis route to regioselectively functionalized bifunctional polyarene

Synthesis route to regioselectively functionalized bifunctional polyarene

Thermal and Optical Properties of Dibenzothiophene-Based Poly(tetramethylsilarylenesiloxane) Derivatives

Nanostructured Organosilicon Luminophores for Effective Light Conversion in Organic Light Emitting Diodes

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