Synthesis and characterization of arylamino end-capped silafluorenes for blue to deep-blue organic light-emitting diodes (OLEDs)

Chen, Shao Fu; Tian, Yuan; Peng, Jinghong; Zhang, Huarong; Feng, Xin Jiang; Zhang, Haixia; Xu, Xinjun; Li, Lidong; Gao, Jianhua

doi:10.1039/c5tc00382b

Cited by 32 publications

(12 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…TLC:Rf (Cyclohexane) = 0.68. Spectroscopic data were in agreement with those reported in the literature [24].…”

supporting

confidence: 90%

“…The silafluorene cores were obtained according to a strategy described in the literature starting with compounds 2-Br. [22,24] Chemoselective halogen-metal exchanges on dibromo-2,2'-diiodobiphenyls 2-Br on iodine atoms with n-BuLi in THF were followed by nucleophilic substitutions on commercial dichlorodimethylsilane. This afforded brominated silafluorenes 3, m-Br and 3, p-Br with good yields, 57 % and 62 % respectively.…”

Section: Synthesismentioning

confidence: 99%

“…This silicon-bridge analog of fluorene has been mainly used for the development of organic light-emitting diodes. [22][23][24] Indeed, silafluorene are much more thermostable than fluorene. Moreover, due to a σ*(Si-C)-π * hyperconjugation effect, the incorporation of silicon atoms into π-conjugated systems is expected to decrease the LUMO energy levels.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Silafluorene as a promising core for cell-permeant, highly bright and two-photon excitable fluorescent probes for live-cell imaging

Auvray

Bolze²,

Clavier

et al. 2021

Dyes and Pigments

View full text Add to dashboard Cite

In this study, we report the synthesis, linear and non-linear photophysical studies and live cell imaging of two two-photon activatable probes based on a silafluorene core: SiFluo-V and SiFluo-L. Thanks to their quadrupolar (A-π-D-π-A) design, these probes exhibit respectively good to impressive two-photon cross sections (from 210 GM to 2150 GM). TD-DFT calculations support the experimental evidence that SiFluo-L displays far better two-photon absorption properties than SiFluo-V. Moreover, SiFluo-L possesses all requirements for bioimaging as it is water soluble, cell-permeant and and presents a low cytotoxicity (IC80≥10 µM). It labels mitochondria in live-cell imaging at low laser power with high brightness, contrast and photostability. This study demonstrates that silafluorene is a promising core to develop new two-photon fluorophores for live cell imaging.

show abstract

“…TLC:Rf (Cyclohexane) = 0.68. Spectroscopic data were in agreement with those reported in the literature [24].…”

supporting

confidence: 90%

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Silafluorene as a promising core for cell-permeant, highly bright and two-photon excitable fluorescent probes for live-cell imaging

Auvray

Bolze²,

Clavier

et al. 2021

Dyes and Pigments

View full text Add to dashboard Cite

show abstract

“…C at 126 MHz, and29 Si at 99.38 MHz) or on a Bruker Avance-300 MHz ( 1 H recorded at 300 MHz,13 C at 75 MHz, and19 F at 282 MHz) at ambient temperature unless otherwise noted). Chloroform-d 1 was purchased from Cambridge Isotopes, Inc.Elemental analyses were performed by Robertson Microlit Labs, Inc., Ledgewood, NJ.…”

mentioning

confidence: 99%

Synthesis and characterization of luminescent 2,7-disubstituted silafluorenes

Hammerstroem

Braddock‐Wilking

Rath

2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

The synthesis and characterization of a series of six new highly fluorescent 2,7alkynyl(aryl)-3,6-dimethoxy-9,9-diphenylsilafluorenes was investigated utilizing a modified multi-step synthetic pathway in which the final step utilizes palladium-catalyzed cross-coupling conditions to incorporate a variety of conjugatedalkynyl(aryl) groups at the 2,7-positions. These new compounds were characterized utilizing X-ray crystallography as well as multinuclear NMR, EA, TGA, DSC, UV-Vis, and fluorescence spectroscopic techniques. The new silafluorene compounds show a strong absorption band in the visible region with a maximum in the region of 374-388 nm and an emission maximum in the range of 403-420 nm. The solution-state quantum efficiencies for the luminescence are high and range from 0.80-0.89. All of the compounds show high thermal stability as determined by DSC and TGA analysis. Conjugated π-electron systems containing silicon have received substantial attention for their use as components for a wide variety of optical and electronic applications such as organic light emitting diodes (OLEDs), photovoltaic devices, field-effect transistors (FETs), and as chemical and biological sensors. 1-18 The unique optoelectronic properties found in these silicon systems arises from the σ*−π* conjugation between the σ* orbital of the two exocyclic groups at the silicon center and π* orbital of the butadiene unit of the ring resulting in a low energy LUMO level. 16,17 Incorporation of conjugated organic moieties on the ring allows for further electronic tuning. 1-22 Silafluorenes represent a relatively new class of photoluminescent molecules which demonstrate smaller band gaps, deep blue emission, high electron affinity, improved thermal stability, and greater quantum yields than that of their fluorene and carbazole analogs. 15,23-30 Silafluorenes are analogs of 9,9-dialkylfluorenes, which have been of interest due to their deep blue emission and their ability to be incorporated into polysilafluorenes. 11,24,26,27,30-37 Commercially available blue emitting polyfluorenes generally have a much shorter lifetime compared to that of red and green emitters. As a result, there has been increased interest in strong blue emitters with high quantum efficiency, lifetime, and color purity. Unfortunately, some polyfluorenes can undergo a decrease in emission and spectral broadening resulting in a low-energy green band over time. 38-40

show abstract

“…The planar structure is required to measure the exact characteristics of the e-jet-printed OLEDs, because nonplanar surfaces (3D features) can distort the direction of light emission or vary the distance between the detector and the light source. [45,46] For example, the maximum current efficiency of the OLED using SPW-111 appears at low current density, but the maximum current efficiency of the other OLED using TBADN:DPAVBi appears at high current density. The plot of current density versus voltage in Figure 4c (Figure 4d), the luminances that were achievable at 12 V for the TBADN:DPAVBi sample and the SPW-111 sample were about 1360 and 1235 cd m −2 , respectively.…”

Section: Wwwadvancedsciencecommentioning

confidence: 99%

High‐Resolution 3D Printing of Freeform, Transparent Displays in Ambient Air

Park

Kim

et al. 2019

Advanced Science

View full text Add to dashboard Cite

show abstract

Synthesis and characterization of arylamino end-capped silafluorenes for blue to deep-blue organic light-emitting diodes (OLEDs)

Abstract: Silafluorene derivatives are designed for blue OLEDs and tunable efficiencies are investigated using end-capped arylamino groups and substituent groups on the silicon atom.

Cited by 32 publications

References 39 publications

Silafluorene as a promising core for cell-permeant, highly bright and two-photon excitable fluorescent probes for live-cell imaging

Silafluorene as a promising core for cell-permeant, highly bright and two-photon excitable fluorescent probes for live-cell imaging

Synthesis and characterization of luminescent 2,7-disubstituted silafluorenes

High‐Resolution 3D Printing of Freeform, Transparent Displays in Ambient Air

Contact Info

Product

Resources

About