Indacenodithienothiophene based chromophore with cyclopentadienylidenehydrazine acceptor moieties

Trainov, Konstantin P.; Salikov, Rinat F.; Platonov, Dmitry N.; Tomilov, Yury V.

doi:10.1016/j.mencom.2020.09.032

Cited by 8 publications

(2 citation statements)

References 26 publications

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“…A new A-D-A chromophore 209 with the indacenodithienothiophene core linked to 2 terminal acceptor hydrazone Cp groups was obtained by the reaction of dilithium indacenodithienothiophene 208 with diazo derivative 206 (Scheme 80) [138].…”

Section: Push−pull Chromophores With Hydrazone Pccp Fragments For Organic Photovoltaicsmentioning

confidence: 99%

Pentacarboxycyclopentadienes in Organic Synthesis

Михайлов¹,

Душенко²

2021

Russ J Org Chem

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The review summarizes the literature data on the synthesis, structure, reactivity, and rearrangements of pentacarboxycyclopentadienes and their derivatives. Their potential for creating new chiral organic catalysts for enantioselective Diels-Alder reactions, cationic polymerization of vinyl ethers, enantioselective protonation of silylenol ethers, aminomethylation, and other processes is described, and aspects of their use as effective carriers of functional groups, new ligand systems for the synthesis of metal complexes and donor-π-acceptor chromophores for organic photovoltaics are considered.

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Section: Push−pull Chromophores With Hydrazone Pccp Fragments For Organic Photovoltaicsmentioning

confidence: 99%

Pentacarboxycyclopentadienes in Organic Synthesis

Михайлов¹,

Душенко²

2021

Russ J Org Chem

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“…It is also viable that the distortion of a seven-membered ring in HMCH is caused by steric hindrance of ester groups which can be disabled in the case of less sterically hindered substituents. Moreover, HMCH was found to exhibit unique reactivity under the action of various nucleophilic and electrophilic agents, yielding a number of functional materials with interesting properties, for example, large Stokes shift superphotoacidic fluorophores. − On the other hand, we have shown that other available cycloheptatrienes containing up to five electron-withdrawing groups neither form a stable anion nor exhibit chemical properties of HMCH . Thus, a new strategy for the synthesis of highly electron-deficient cycloheptatrienes will be of high demand from both theoretical and applicative points of view.…”

Section: Introductionmentioning

confidence: 99%

Cascade Vinylation/8π-Electrocyclization and Cu(II)-Catalyzed Dehydrogenation toward Highly Stable Formally Antiaromatic Cycloheptatrienyl Anions

et al. 2023

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An approach to the synthesis of seven-membered systems via the chain elongation of nucleophilic propenes and subsequent 8π-electrocyclization is proposed. The cascade reaction yields either cycloheptadienes or bicycloheptenes, and the latter are formed via a 6π-electrocyclization of intermediate cycloheptadienyl anion which was proved to be reversible in a basic medium. The electrocyclic nature of the ring-closing reactions was supported by density functional theory and DLPNO/CCSD(T) calculations. Highly electron-deficient cycloheptatrienes can be obtained from cycloheptadienes or bicycloheptenes via oxidation either introduced into the cascade reaction or performed as a separate reaction, with the overall yield of up to 81%. The oxidation step was performed by means of a rarely encountered Cu(II)-catalyzed dehydrogenation of cycloheptadienes or bicycloheptenes, and so the reaction mechanism was proposed. Stable formally 8π-antiaromatic cycloheptatrienyl-anion containing compounds were obtained, and some correlations between their UV−vis spectra and the structure of the distorted cycloheptatrienyl-anion moiety were clarified. Additionally, a base-induced retro-[2 + 2]-cycloaddition in a bicycloheptene derivative gave cyanotetra-(methoxycarbonyl)cyclopentadienyl cesium.

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