Benzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole) and Its Bromo Derivatives: Molecular Structure and Reactivity

Chmovzh, T.N.; Alekhina, D.A.; Kudryashev, T.A.; Aysin, R.R.; Korlyukov, A.A.; Rakitin, O.A.

Авторы: Chmovzh T.N., Alekhina D.A., Kudryashev T.A., Aysin R.R., Korlyukov A.A., Rakitin O.A.
Журнал: International Journal of Molecular Sciences
Том: 24
Год издания: 2023
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 8835
DOI: 10.3390/ijms24108835
Аннотация: Benzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole) (isoBBT) is a new electron-withdrawing buildingblock that can be used to obtain potentially interesting compounds for the synthesis of OLEDsand organic solar cells components. The electronic structure and delocalization in benzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole), 4-bromobenzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole), and 4,8-dibromobenzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole) were studied using X-ray diffraction analysis and ab initio calculationsby EDDB and GIMIC methods and were compared to the corresponding properties of benzo[1,2-c:4,5-c0]bis[1,2,5]thiadiazole (BBT). Calculations at a high level of theory showed that the electron affinity,which determines electron deficiency, of isoBBT was significantly smaller than that of BBT (1.09vs. 1.90 eV). Incorporation of bromine atoms improves the electrical deficiency of bromobenzo-bisthiadiazolesnearly without affecting aromaticity, which increases the reactivity of these compoundsin aromatic nucleophilic substitution reactions and, on the other hand, does not reduce the ability toundergo cross-coupling reactions. 4-Bromobenzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole) is an attractiveobject for the synthesis of monosubstituted isoBBT compounds. The goal to find conditions for theselective substitution of hydrogen or bromine atoms at position 4 in order to obtain compounds containinga (het)aryl group in this position and to use the remaining unsubstituted hydrogen or bromineatoms to obtain unsymmetrically substituted isoBBT derivatives, potentially interesting compoundsfor organic photovoltaic components, was not set before. Nucleophilic aromatic and cross-couplingreactions, along with palladium-catalyzed C-H direct arylation reactions for 4-bromobenzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole), were studied and selective conditions for the synthesis of monoarylatedderivatives were found. The observed features of the structure and reactivity of isoBBT derivativesmay be useful for building organic semiconductor-based devices.
Добавил в систему: Айсин Ринат Равильевич

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№	Имя	Описание	Имя файла	Размер	Добавлен
1.	Полный текст		2023_ijms_Rakitin.pdf	6,0 МБ	16 мая 2023 [arinatr]
2.	Экспертное заключение		IMG_20230518_0001.pdf	558,0 КБ	18 мая 2023 [arinatr]

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Benzo[1,2-d:4,5-d0]bis([1,2,3]thiadiazole) and Its Bromo Derivatives: Molecular Structure and Reactivityстатья

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