Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds
Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds
复制标题
DOI：
10.2494/photopolymer.30.561
复制
发表时间：
2017-01-01
影响因子：
0.8
通讯作者：
Wakamiya, Atsushi
中科院分区：
文献类型：
--
作者：
Nakamura, Tomoya;Okazaki, Shuhei;Wakamiya, Atsushi
2,1,3-苯并噻唑（BT）是一种广泛应用于有机电子器件，包括有机太阳能电池（OSCs）的电子接受单元。作为BT骨架的修饰，设计并合成了两种类型的噻唑熔融BT单元；噻唑熔融BT具有吸电子的C=N键，咪唑熔融BT具有供电子的氮原子和吸电子的C=N键。电化学测量和理论计算表明，噻唑融合增强了BT骨架的电子接受能力，而咪唑融合使BT骨架在保持电子接受能力的同时具有给电子能力。此外，在噻唑熔接BT单元中，通过改变熔接噻唑环上甲基硫基中硫原子的氧化态，可以进一步调节电子结构。
2,1,3-Benzothiadiazole (BT) is a widely used electron-accepting unit in organic electronics including organic solar cells (OSCs). As modifications of BT skeleton, two types of azole-fused BT units were designed and synthesized; thiazole-fused BT with an electron withdrawing C=N bond and imidazole-fused BT with an electron-donating nitrogen atom as well as an electron-withdrawing C=N bond. Electrochemical measurements and theoretical calculations suggest that thiazole-fusion enhances the electron-accepting ability, whereas imidazole-fusion endows the BT skeleton with electron-donating ability while maintaining its electron-accepting ability. Moreover, in thiazole-fused BT units, the electronic structure could be further modulated by varying the oxidation state of the sulfur atom in methylthio group at the fused thiazole ring.