Ultraviolet-emitting conjugated polymer poly(9,9′-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV

Mo, Yueqi; Tian, Rong; Shi, Wei; Cao, Yong

doi:10.1039/b507518a

Cited by 94 publications

(73 citation statements)

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“…Different synthetic routes had been introduced to prepare 16 and 18 by us and Holmes's group, from which some 3,6-difunctional monomers 17, 19, and 20 were thus obtained. [79,80,89] The Pd(OAc) 2 /tricyclohexylphosphine-catalyzed Suzuki coupling reaction of 12 and 13 readily afforded the phenyl group end-capped poly(2,7-dibenzosilole) 21 in a high yield of 93% (Scheme 5). [78] The M w and M n of 21 were 220 000 and 31 000, respectively, giving a DP of %90.…”

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confidence: 99%

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Silole‐Containing Polymers: Chemistry and Optoelectronic Properties

Chen

Cao

2007

Macromol. Rapid Commun.

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334

139

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In this review, the synthesis and optoelectronic properties of various π‐conjugated‐, σ‐conjugated‐, pendanted‐, and hyperbranched or dendritic silole‐containing polymers (SCPs) are described. So far, substituted silole, dibenzosilole, dithienosilole, and bis‐silicon‐bridged stilbene have been incorporated into SCPs. The tunable bandgaps from 4.0–1.55 eV, variable fluorescent colors from UV to blue, green, and red (RGB) light, fluorescent chemo‐sensors for 2,4,6‐trinitrotoluene (TNT)‐type explosives, aggregation‐induced emission, efficient electroluminescence emissions for RGB lights, phosphorescent hosts with high triplet energy level, efficient solar cells, stable field‐effect transistors with high hole mobility in air, and attenuation of strong laser power, are the important features of SCPs.

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“…[79] The M w and M n of 22a with two hexyl substituents at the silicon atom were 16 000 and 10 000, respectively. This Reprinted with permission from ref.…”

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Silole‐Containing Polymers: Chemistry and Optoelectronic Properties

Chen

Cao

2007

Macromol. Rapid Commun.

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334

139

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“…Thus, we selected as eries of symmetrically substituted [5,5'-diamino-(2b); [22] 5,5'-dichloro-(2c); [21] and unsymmetrically substituted [4-chloro-(2d)a nd 4-methyl-2,2'dibromobiphenyl (2e) [23] ]2,2'-dibromobiphenyls. Direct manipulationo fc ommercial 2,2'-dibromobiphenyl led to symmetrically substituted derivatives 2b and 2c.A na utotandem reaction on 2,2'-dibromo-5,5'-dichlorobiphenyl 2c led to the desired substituted spirofluorenes 5b and 5c,a lbeit with moderate to poor yields (Scheme 6).…”

Section: Resultsmentioning

confidence: 99%

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Barroso

Cabal

Badía‐Laiño

et al. 2015

Chemistry A European J

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The Pd-catalyzed reaction between 2,2'-dibromobiphenyls and related systems with tosylhydrazones gives rise to new π-extended conjugated polycarbo- and heterocycles through an autotandem process involving a cross-coupling reaction followed by an intramolecular Heck cyclization. The reaction shows wide scope regarding both coupling partners. Cyclic and acyclic tosylhydrazones can participate in the process. Additionally, a variety of aromatic and heteroaromatic dibromoderivatives have been employed, leading to an array of diverse scaffolds featuring a fluorene or acridine central nucleus, and containing binaphthyl, thiophene, benzothiophene and indole moieties. The application to appropriate tetrabrominated systems led to greater structural complexity through two consecutive autotandem cascades. The photophysical properties of selected compounds were studied through their absorption and emission spectra. Fluorescence molecules featuring very high quantum yields were identified, showing the potential of this methodology in the development of molecules with interesting optoelectronic properties.

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“…The alternating copolymers of 3,6-dibenzosilole all showed higher energy gaps than the 2,7-substituted analogues, consistent with the previous findings for the two homopolymers. 24,[31][32] Copolymers containing triarylamine (P4 and P8) and carbazole (P1 and P5) subunits have higher absorption onset wavelengths and consequently smaller energy gaps, implying a greater degree of conjugation within these materials. When considering the difference in optical energy gap (ΔEg), observed when the dibenzosilole is linked through '2,7'-or '3,6'-positions, the data shows an increase with co-monomer in the order: triarylamine < carbazole < oxadiazole < triazole.…”

Section: Characterisation and Photophysical Measurementsmentioning

confidence: 99%

“…[31][32] The material reported by Cao and co-workers was formed by a nickelcatalysed coupling reaction and was noted to possess a wide HOMO-LUMO gap of approximately 4.0 eV. 32 Our group prepared an end-capped poly(9,9-dialkyl-3,6-dibenzosilole) homo-polymer, via a Suzuki polycondensation, which was highly soluble in common organic solvents. 31 The high energy gap of this material (calculated to be 3.5 eV), was put to use as a host material for a phosphorescent iridium guest complex.…”

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The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

et al. 2011

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An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics.To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials, by the respective combination of either a 3,6-or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-dibromo-N-octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised, using 1 H, 13 C{ 1 H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' Keyworth et al., 'The tuning of the energy levels of dibenzosilole copolymers....' 2 HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration:glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence.The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 x 10 -4 cm 2 V -1 s -1 and current on/off ratios of 10 5 .

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Ultraviolet-emitting conjugated polymer poly(9,9′-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV

Abstract: An ultraviolet-emitting conjugated polymer, poly(9,9'-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV, has been synthesized and characterized.

Cited by 94 publications

References 26 publications

Silole‐Containing Polymers: Chemistry and Optoelectronic Properties

Silole‐Containing Polymers: Chemistry and Optoelectronic Properties

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

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