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

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Abstract

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.

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About the authors

I. O. Gudkova

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

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

E. A. Sorokina

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

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

Е. А. Zaborin

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

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

M. S. Polinskaya

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

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

О. V. Borshchev

Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences

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

S. А. Ponomarenko

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

Author for correspondence.
Email: ponomarenko@ispm.ru

Lomonosov Moscow State University, Faculty of Chemistry

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

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Supplementary files

Supplementary Files
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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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