Star-Shaped D-π-A Conjugated Molecules: Synthesis and Broad Absorption Bands

Wang, Jinliang; Tang, Zhengming; Xiao, Qi; Ma, Yuguo; Pei, Jian

doi:10.1021/ol802845w

Cited by 46 publications

(25 citation statements)

References 43 publications

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“…[21] In this system, truxene acts as the core, connecting the D branch of the triphenylamine (TPA) unit and the A branch of the functionalized benzothiadiazole moiety. After the introduction of A groups, the absorption bands of the star-shaped molecules become broader and stronger in the range of 250 to 700 nm, which covers the whole visible region.…”

Section: Star-shaped Aromaticsmentioning

confidence: 99%

π‐Conjugated Aromatics Based on Truxene: Synthesis, Self‐Assembly, and Applications

Shi

Wang

Pei

2014

The Chemical Record

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Recently, many efforts have been devoted to developing novel polycyclic aromatics due to their unique optical and electronic properties and broad applications, such as in organic field-effect transistors, organic photovoltaics, and organic light-emitting diodes. Among various π-conjugated molecules, many truxene derivatives have interesting characteristics such as C3 -symmetry, strong blue emission, and a planar rigid structure. Moreover, compared with many other π-conjugated aromatics, the synthesis and modification of truxene are particularly facile and diverse. In this account, we summarize investigations into truxene derivatives from synthesis and physical properties to applications in organic electronics.

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Section: Star-shaped Aromaticsmentioning

confidence: 99%

π‐Conjugated Aromatics Based on Truxene: Synthesis, Self‐Assembly, and Applications

Shi

Wang

Pei

2014

The Chemical Record

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“…Riobé et al have demonstrated that a 1,3,5‐triazine acceptor appended with two tetrathiafulvalene (TTF) donors has a lower‐energy charge‐transfer (CT) absorption band than the homologous mono‐appended system, EPR spectroscopy having demonstrated that the two TTF donors act independently of one another . Wang et al have reported unsymmetrical D–A motifs in which either one triarylamine (TAA) donor and two benzothiadiazole (BTD) acceptors, or vice versa, are appended to a truxene core . They demonstrated that increasing the acceptor character of the molecules broadens and intensifies the CT absorption bands in both solution and thin films.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of Unsymmetrically Substituted Triarylamine Hexaazatrinaphthalenes

et al. 2017

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We report herein the synthesis and optical properties of unsymmetrically substituted hexaazatrinaphthalene (HATN) systems, and the influence of donor additivity on the electronic properties of the material. The hexaazatrinaphthalenes have been studied by means of electrochemical, electronic absorption and emission, FT Raman and resonance Raman methodologies coupled with DFT calculations. The optical spectra are dominated by low‐energy charge‐transfer states, which show a redshift of excitation energy of around 0.1 eV and an increase in ε of around 125 % as the number of donors is increased. The emission spectra exhibit significant solvatochromism, with Lippert–Mataga analysis yielding Δµ values between 34 and 60 D.

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“…[17] Dendrimer G0-2-1 was obtained in 64 % yield through a threefold WittigHorner reaction between trialdehyde 4 [15] and phosphonate 3. [18] Reduction of (E)-5-(2-(thiophen-2-yl)vinyl)thiophene-2-carbaldehyde with NaBH 4 gave 5 in 97 % yield.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Solution‐Processed Bulk Heterojunction Photovoltaic Cells from Gradient π‐Conjugated Thienylene Vinylene Dendrimers

Wang

Zhong

Tang

et al. 2009

Chemistry An Asian Journal

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A series of gradient π‐conjugated dendrimers and their corresponding models based on 5,5,10,10,15,15‐hexahexyltruxene moieties as nodes and oligo(thienylene vinylene) (OTVs) units with different lengths as branching arms are synthesized in good yields through Wittig–Horner reactions. All new compounds are fully characterized by 1H and 13C NMR spectroscopy, elemental analysis, and MALDI‐TOF MS or ESI‐MS. Investigation of their photophysical properties reveals that the gradient dendritic scaffold not only results in a higher molar absorption coefficient and broader absorption region than those of their corresponding model compounds, but also improves the PL quantum yields relative to the corresponding OTVs. The suitable HOMO and LUMO levels as well as excellent film forming properties make these molecules potential candidates for organic solar cells. Solution‐processed bulk heterojunction solar cells using these dendrimers as donor and [6,6]‐phenyl‐C61 butyric acid methyl ester as acceptor are prepared and tested. The power conversion efficiency of the devices based on G0-4-2 is 0.40 % under illumination of air mass 1.5 and 100 mW cm−2. This is the highest record value for OTV‐based materials to date. Although the absorption band of dendrimer G0-4-2 is much narrower than that of poly(3‐hexylthienylene vinylene) (P3HTV), the efficiency of its solar cell device is almost twice that of the device based on P3HTV. This result shows clearly the advantage of gradient dendritic structures as active materials for photovoltaic cells.

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Star-Shaped D-π-A Conjugated Molecules: Synthesis and Broad Absorption Bands

Cited by 46 publications

References 43 publications

π‐Conjugated Aromatics Based on Truxene: Synthesis, Self‐Assembly, and Applications

π‐Conjugated Aromatics Based on Truxene: Synthesis, Self‐Assembly, and Applications

Synthesis and Optical Properties of Unsymmetrically Substituted Triarylamine Hexaazatrinaphthalenes

Solution‐Processed Bulk Heterojunction Photovoltaic Cells from Gradient π‐Conjugated Thienylene Vinylene Dendrimers

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