Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction

Lin, Yi‐Chun; Lin, Chih‐Hsiu; Chen, Chan-Yu; Sun, Shih‐Sheng; Pal, Bikash C.

doi:10.1039/c0ob00575d

Cited by 29 publications

(24 citation statements)

References 44 publications

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“…NMR spectrum of the solid was in accordance with the previously reported spectrum of the compound. 18 Full evaporation of the solvent and drying in vacuo afforded TCNA with some impurities of pinacol (approx. 3 m% based on 1 H NMR spectra), which could not be removed due to the difficult redissolution of TCNA.…”

Section: Resultsmentioning

confidence: 99%

“…For testing and demonstrating this approach, we selected TCNA as the target compound. This anthracene derivative was prepared previously by a related monodirectional elongation approach, 18 which we expected to facilitate the identification of the compound in our reactions and, hence, the evaluation of our double ring-closing approach. Exceptionally low solubility was reported for TCNA in the previous work, making it a particularly challenging target compound for any preparation method.…”

Section: Introductionmentioning

confidence: 99%

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Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

et al. 2020

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Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach. File list (3) download file view on ChemRxiv Draft_final.pdf (351.19 KiB) download file view on ChemRxiv SI_final.pdf (550.08 KiB) download file view on ChemRxiv all.cif (559.68 KiB)

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

et al. 2020

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“…The naphthalene and anthraceneimide dimers, 2 and 3 a-3 e, were obtained from the corresponding tetraaldehyde 5 or 6 and N-alkyl or N-arylmaleimide in the moderate yields of 23-33 % by using the bidirectional acene elongation reaction reported by Lin et al (see the Supporting Information). [12]…”

Section: Synthesismentioning

confidence: 99%

Hybridization of a Flexible Cyclooctatetraene Core and Rigid Aceneimide Wings for Multiluminescent Flapping π Systems

Yuan

Saito

Camacho

et al. 2014

Chemistry A European J

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The hybridization of flexible and rigid π-conjugated frameworks is a potent concept for producing new functional materials. In this article, a series of multifluorescent flapping π systems that combine a flexible cyclooctatetraene (COT) core and rigid aceneimide wings with various π-conjugation lengths has been designed and synthesized, and their structure/properties relationships have been investigated. Whereas these molecules have a V-shaped bent conformation in the ground state, the bent structure changes to a planar conformation in the lowest excited singlet (S1 ) state irrespective of the lengths of the aceneimide wings. However, the fluorescence behavior in solution is distinct between the naphthaleneimide system and the anthraceneimide system. The former has a nonemissive S1 state owing to the significant contribution of the antiaromatic character of the planar COT frontier molecular orbitals, thereby resulting in complete fluorescence quenching in solution. In contrast, the latter anthraceneimide system shows an intense emission, which is ascribed to the planar but distorted S1 state that shows the allowed transition between the π-molecular orbitals delocalized over the COT core and the acene wings. The other characteristic of these π systems is the significantly redshifted fluorescence in the crystalline state relative to their monomer fluorescence. The relationship between the packing structures and the fluorescence properties was investigated by preparing a series of hybrid π systems with different sizes of substituents on the imide moieties, which revealed the effect of the twofold π-stacked structure of the V-shaped molecules on the large bathochromic shift in emission.

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“…[ 159 – 165 ]. Moreover, the literature known methods adopted mainly harsh reaction condition and they are generally found to be low yielding [ 166 – 168 ]. Recently, Mal and co-workers reported mechanochemical synthesis of hetero-acenes from 1,2-dicarbonyl compounds and 1,2-diaminoarenes using 10 mol % p -toluenesulfonic acid as catalyst.…”

Section: Reviewmentioning

confidence: 99%

Mechanochemical synthesis of small organic molecules

Achar

Bose

Mal

2017

Beilstein J. Org. Chem.

239

111

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With the growing interest in renewable energy and global warming, it is important to minimize the usage of hazardous chemicals in both academic and industrial research, elimination of waste, and possibly recycle them to obtain better results in greener fashion. The studies under the area of mechanochemistry which cover the grinding chemistry to ball milling, sonication, etc. are certainly of interest to the researchers working on the development of green methodologies. In this review, a collection of examples on recent developments in organic bond formation reactions like carbon–carbon (C–C), carbon–nitrogen (C–N), carbon–oxygen (C–O), carbon–halogen (C–X), etc. is documented. Mechanochemical syntheses of heterocyclic rings, multicomponent reactions and organometallic molecules including their catalytic applications are also highlighted.

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Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction

Cited by 29 publications

References 44 publications

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Hybridization of a Flexible Cyclooctatetraene Core and Rigid Aceneimide Wings for Multiluminescent Flapping π Systems

Mechanochemical synthesis of small organic molecules

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