Substitution degree engineering the crystal packing and optoelectronic properties of benzofuranvinyl-substituted benzene-cored derivatives

Qiu, Jin-Xing; Li, Ye-Xin; Yang, Xiaofeng; Nie, Yong; Zhang, Zhenwei; Chen, Zhonghe; Sun, Guangmin

doi:10.1039/c4tc00220b

Cited by 28 publications

(15 citation statements)

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“…More specifically, interest in several natural and synthetic 2‐aroylbenzofurans has risen because of their broad spectrum of biological effects, including antifungal, antibacterial, antileishmanial, antioxidant, anti‐HIV, antitumor, anti‐inflammatory, antiproliferative, and cytotoxic actions . In addition, some 2‐aroylbenzufuran derivatives can be used as sensors and semiconductors and as probes for β‐amyloid plaques in Alzheimer's disease …”

Section: Introductionmentioning

confidence: 99%

Fragmentation of 2‐aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry

et al. 2017

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We investigated the gas-phase fragmentation reactions of a series of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The most intense fragment ions were the acylium ions m/z 105 and [M+H-C H ] , which originated directly from the precursor ion as a result of 2 competitive hydrogen rearrangements. Eliminations of CO and CO from [M+H-C H ] were also common fragmentation processes to all the analyzed compounds. In addition, eliminations of the radicals •Br and •Cl were diagnostic for halogen atoms at aromatic ring A, whereas eliminations of •CH and CH O were useful to identify the methoxyl group attached to this same ring. We used thermochemical data, obtained at the B3LYP/6-31+G(d) level of theory, to rationalize the fragmentation pathways and to elucidate the formation of E, which involved simultaneous elimination of 2 CO molecules from B.

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Section: Introductionmentioning

confidence: 99%

Fragmentation of 2‐aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry

et al. 2017

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“…Generally, the emission of the π-conjugated molecules would be red-shifted with reduced quantum yield when the molecules largely stack in aggregated states. π-Conjugated systems with relatively flexible framework such as oligo(phenylene vinylene) have been chosen to reveal the impact of conformation on emission 34 35 . Indeed, plenty of molecules have been constructed regarding the structure-property relationship 36 37 38 39 .…”

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confidence: 99%

Emission behaviors of unsymmetrical 1,3-diaryl-β-diketones: A model perfectly disclosing the effect of molecular conformation on luminescence of organic solids

Cheng

Han

et al. 2015

Sci Rep

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A series of unsymmetrical 1,3-diaryl-β-diketones 1–6 displaying molecular conformation-dependent fluorescence quantum yields have been synthesized. Crystals with planar molecular conformation such as 1, 2, 3 and 4 are highly fluorescent (φf: 39–53%), and the one holding slightly twisted conformation (5) is moderately luminescent (φf = 17%), while crystal 6 possessing heavily bent structure is completely nonluminous (φf ~ 0). The distinct fluorescence efficiencies are ascribed to their different molecular conformations, since all the crystals hold the same crystal system, space group and crystal packing structures. Additionally, the fluorescent crystals 1–5 display low threshold amplified spontaneous emission (ASE) with small full widths at half-maximum (FWHM: 3–7 nm), indicating their potential as candidates for organic crystal lasing devices.

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“…[20,21,22] Moreover, linear extended benzofuran derivatives are efficient luminophores presenting high quantum yield both in solution and in the solid state. [23,24] In the continuation of our current interest in conjugated systems based on benzofuran units, we have prepared and explored the electronic properties of two new series of derivatives associating benzofuran-cyanovinyl unit with phenyl or furan moieties obtained from benzaldehyde-lignocellulosic (Be1-Be3) or furaldehyde -saccharide (Fu1-Fu2) platforms (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Benzofuran based semiconductors have been investigated in OFET and solar cell devices [20,21,22] . Moreover, linear extended benzofuran derivatives are efficient luminophores presenting high quantum yield both in solution and in the solid state [23,24] …”

Section: Introductionmentioning

confidence: 99%

Exploring the Electronic Properties of Extended Benzofuran‐Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

et al. 2021

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Two series of linear extended benzofuran derivatives associating cyanovinyl unit and phenyl or furan moieties obtained from benzaldehyde-lignocellulosic (Be series) or furaldehyde-saccharide (Fu series) platforms were prepared in order to investigate their emission and electrochemical properties. For the fluorescence in solution and solid states, contrasting results between the two series were demonstrated. For Be series a net aggregation induced emission effect was observed with high fluorescence quantum yield for the solid state. A [2 + 2] cycloaddition under irradiation at 350 nm was also revealed for one derivative of Be series. In contrast, for Fu series the fluorescence in solution is higher than in the solid state. The X-ray crystallography studies for the compounds reveal the formation of strong π-π stacking for the derivatives without emissive property in the solid state and the presence of essentially lateral contacts for emissive compounds. Taking advantage of the propensity to develop 2D π-stacking mode for the more extended derivative with a central furan cycle, organic field effect transistors presenting hole mobility have been made.

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Substitution degree engineering the crystal packing and optoelectronic properties of benzofuranvinyl-substituted benzene-cored derivatives

Abstract: The molecular shape exerts remarkable effects on solubility, polymorphism, crystal packing and optoelectronic properties – searching for 3D organic semiconductors.

Cited by 28 publications

References 50 publications

Fragmentation of 2‐aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry

Fragmentation of 2‐aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry

Emission behaviors of unsymmetrical 1,3-diaryl-β-diketones: A model perfectly disclosing the effect of molecular conformation on luminescence of organic solids

Exploring the Electronic Properties of Extended Benzofuran‐Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

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