Planar [6]Radialenes: Structure, Synthesis, and Aromaticity of Benzotriselenophene and Benzotrithiophene

Patra, Asit; Wijsboom, Yair H.; Shimon, Linda J. W.; Bendikov, Michael

doi:10.1002/anie.200703123

Cited by 45 publications

(26 citation statements)

References 54 publications

(49 reference statements)

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“…[12b, 15b] An alternative approach to conjugated materials with unprecedented properties is heteroelement incorporation.T he use of main group elements as p-type dopants has recently led to extraordinary examples of p-conjugated materials with small bandgaps [16] and materials with interesting bonding situations. [17] Especially the chemistry of organophosphorus p-conjugated materials has seen considerable development in recenty ears, with the synthesis of novel P-based conjugated compounds andt he elucidation of their optical and electrochemicalp roperties. [16d, 18] Fascinatingp hosphaalkene architectures have been prepared and investigated, such as ab enzene with multiple phosphaethenes ubstituents, [19] linear poly-and oligomers, [20] and radialenes [21] with endo-and exotopic phosphaalkeneu nits.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Electronic Properties of Acetylenic Fluorenes by Phosphaalkene Incorporation

Svyaschenko

Orthaber

Ott

2016

Chemistry A European J

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Versatile synthetic protocols for 2,7- and 3,6-diacetylenic fluorene-9-ylidene phosphanes (F9Ps) were developed. Protodesilylation of trimethylsilyl-protected acetylenic F9Ps affords terminal acetylenes that can be employed in Sonogashira and Glaser-type C-C coupling reactions to give thienyl-decorated and butadiyne-bridged fluorene-9-ylidene phosphanes, respectively. As evidenced by UV/Vis spectroscopy and cyclic voltammetry and corroborated by ab initio calculations, the presence of the P center in the F9Ps induces a significantly reduced HOMO-LUMO splitting that originates from stabilization of the LUMO levels. Variation of the acetylene substitution pattern is an additional tool to influence the optical and electronic properties. Whereas 3,6-disubstituted F9Ps have strong absorptions around 400 nm, mainly due to π-π* transitions, 2,7-diacetylenic F9Ps exhibit longest-wavelength absorptions that have significant charge-transfer character with an onset around 520 nm.

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Section: Introductionmentioning

confidence: 99%

Tuning the Electronic Properties of Acetylenic Fluorenes by Phosphaalkene Incorporation

Svyaschenko

Orthaber

Ott

2016

Chemistry A European J

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“…[2] Recently,d ifferent planar central cores involving three thiophene rings fused to an arene ring (trithienobenzenes;B TTs) have been described. [3] Owing to their electron-rich nature,B TTsc an serve as donor units in the design of severalo ptoelectronic devices. In addition, the coplanarity and extended p-conjugation of the BTT skeleton should promote intermolecular p-stacking, which wouldi nduce stronga ggregation and enhanced solid-state packing in BTT-containing systems.…”

Section: Introductionmentioning

confidence: 99%

Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks: The Effect of Star‐Shaped versus Linear Conjugation on Their Electronic Structures

Riaño

Arrechea‐Marcos

Mancheño

et al. 2016

Chemistry A European J

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The synthesis, characterization, and optical properties of a novel star-shaped oligothiophene with a central rigid trithienobenzene (BTT) core and diketopyrrolopyrrole (DPP) units are reported and compared with homologous linear systems based on the benzodithiophene (BDT) and the naphthodithiophene (NDT) units end capped with DPPs. This comparison is aimed at elucidating the effect of the star-shaped configuration versus linear conformation on the optical and electrical properties. Electronic and vibrational spectroscopies, together with transient absorption spectroscopy, scanning electronic microscopy, and DFT calculations are used to understand not only the molecular properties of these semiconductors, but also to analyze the supramolecular aggregation in these derivatives. We conclude that although the subject star-shaped derivative is not optimal in terms of π-conjugation, its extended BTT unit significantly favors intermolecular π-stacking interactions, which is interesting for their applications in devices. Field-effect transistors and solar cells were fabricated with these new molecular semiconductors and the performance difference discussed.

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“…As presented in Figure , the 17 compounds are ranked based on the number of Se atoms while the 13 – 17 are listed at last. For the crystal structures, it can be categorized into five types based on their packing symmetry elements . The first also the simplest one is the material with molecules in transfer layers stacking as central symmetry, which includes 4 , 9 , 11 – 17 .…”

Section: Resultsmentioning

confidence: 99%

“…For the crystal structures, it can be categorized into five types based on their packing symmetry elements. [29,[54][55][56][57][58][59][60][61][62][63][64][65] The first also the simplest one is the material with molecules in transfer layers stacking as central symmetry, which includes 4, 9, 11-17. The second kind consists Compounds are same to previously investigated system which is isomer of Compounds 4.…”

Section: Crystal and Geometric Structuresmentioning

confidence: 99%

Anisotropic charge carrier transport of optoelectronic functional selenium‐containing organic semiconductor materials

et al. 2020

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Organic semiconductors (OSCs) materials are currently under intense investigation because of their potential applications such as organic field‐effect transistors, organic photovoltaic devices, and organic light‐emitting diodes. Inspired by the selenization strategy can promote anisotropic charge carrier migration, and selenium‐containing compounds have been proved to be promising materials as OSCs both for hole and electron transfer. Herein, we now explore the anisotropic transport properties of the series of selenium‐containing compounds. For the compound containing SeSe bond, the SeSe bond will break when attaching an electron, thus those compounds cannot act as n‐type OSCs. About the different isomer compounds with conjugated structure, the charge transfer will be affected by the stacking of the conjugated structures. The analysis of chemical structure and charge transfer property indicates that Se‐containing materials are promising high‐performance OSCs and might be used as p‐type, n‐type, or ambipolar OSCs. Furthermore, the symmetry of the selenium‐containing OSCs will affect the type of OSCs. In addition, there is no direct relationship between the R groups with their performance, whether it or not as p‐type OSCs or n‐types. This work demonstrates the relationship between the optoelectronic function and structure of selenium‐containing OSCs materials and hence paves the way to design and improve optoelectronic function of OSCs materials.

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Planar [6]Radialenes: Structure, Synthesis, and Aromaticity of Benzotriselenophene and Benzotrithiophene

Cited by 45 publications

References 54 publications

Tuning the Electronic Properties of Acetylenic Fluorenes by Phosphaalkene Incorporation

Tuning the Electronic Properties of Acetylenic Fluorenes by Phosphaalkene Incorporation

Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks: The Effect of Star‐Shaped versus Linear Conjugation on Their Electronic Structures

Anisotropic charge carrier transport of optoelectronic functional selenium‐containing organic semiconductor materials

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