Peculiarities of the ketogroup reduction in the synthesis of mono- and dialkyl-substituted derivatives of benzo[b]benzo[4,5]-thieno[2,3-d]thiophene

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

Mono- and dioctyl-substituted benzo[b]benzo[4,5]-thieno[2,3-d]thiophene derivatives, C8-BTBT and C8-BTBT-C8, have been synthesized, widely used as organic semiconductors for the manufacture of various organic electronics devices. The preparation of target molecules was carried out in 2 stages: acylation of BTBT according to Friedel—Crafts and subsequent reduction of the ketogroup. Since the rate-limiting step in the preparation of such compounds is reduction, various approaches to the reduction of acyl-substituted BTBT derivatives have been investigated and possible mechanisms for these reactions have been proposed. It has been shown that the most effective reduction occurs using hydrazine hydrate.

Толық мәтін

Рұқсат жабық

Авторлар туралы

I. Gudkova

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

Email: ponomarenko@ispm.ru
Ресей, ul. Profsoyuznaya, 70, Moscow, 117393

E. Sorokina

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

Email: ponomarenko@ispm.ru
Ресей, ul. Profsoyuznaya, 70, Moscow, 117393

Е. Zaborin

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

Email: ponomarenko@ispm.ru
Ресей, ul. Profsoyuznaya, 70, Moscow, 117393

M. Polinskaya

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

Email: ponomarenko@ispm.ru
Ресей, ul. Profsoyuznaya, 70, Moscow, 117393

О. Borshchev

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

Email: ponomarenko@ispm.ru
Ресей, ul. Profsoyuznaya, 70, Moscow, 117393

S. Ponomarenko

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences; Lomonosov Moscow State University

Хат алмасуға жауапты Автор.
Email: ponomarenko@ispm.ru

Lomonosov Moscow State University, Faculty of Chemistry

Ресей, ul. Profsoyuznaya, 70, Moscow, 117393; Leninskie gory, 1/3, Moscow, 119991

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Әрекет
1. JATS XML
Жүктеу
2. Scheme 1. Mono- and diacylation of BTBT according to Friedel-Crafts

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3. Fig. 1. GPC curves of compounds 2 (a) and 3 (b). In the chromatogram (b), the leftmost peak corresponds to the by-product of substitution at positions 3 and 8 of the BTBT nucleus. The abscissa axis shows time, min; the ordinate axis shows the optical density of the substance, mAU.

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4. Scheme 2. Synthesis of the target compound C8-BTBT-C8 (a) and by-products 4, 5 isolated from the reaction mass after synthesis (b).

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5. Scheme 3. Proposed mechanism of the reduction reaction of compound 2 in a mixture of NaBH4 and AlCl3.

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6. Fig. 2. Fragment of the 1H NMR spectrum of the mixture of C8-BTBT-C8 and intermediate product 4 with characteristic signals (a); fragment of the absorption spectrum of the by-product 4 with a double bond (left) and the absorption spectrum of the target C8-BTBT-C8 (right) (b). The abscissa axis shows the wavelength, nm; the ordinate axis shows the absorption intensity, rel. units.

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7. Scheme 4. Restoration of the double bond in compound 4

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8. Fig. 3. Fragment of the 1H NMR spectrum of alcohol 5 – 1,1'-(benzo[b]benzo[4,5]thieno[2,3-d]thiophene-2,7-diyl)bis(octan-1-ol)

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9. Scheme 5. Proposed mechanism of the reduction reaction of compound 2 using the Kizhner-Wolf method.

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10. Scheme 6. Synthesis of the compound C8-BTBT

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11. Scheme 7. Proposed mechanism of the reduction reaction of compound 3 in a mixture of LiAlH4, AlCl3

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