A Facile Synthesis of Low-Band-Gap Donor-Acceptor Copolymers Based on Dithieno[3,2-b:2′,3′-d]thiophene

被引:29
作者
Ku, Sung-Yu [1 ,4 ]
Liman, Christopher D. [1 ,2 ,4 ]
Burke, Daniel J. [1 ,3 ]
Treat, Neil D. [1 ,2 ,3 ]
Cochran, Justin E. [1 ,3 ]
Amir, Elizabeth [1 ,4 ]
Perez, Louis A. [1 ,2 ]
Chabinyc, Michael L. [1 ,2 ,4 ]
Hawker, Craig J. [1 ,2 ,3 ,4 ,5 ]
机构
[1] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA
[2] Univ Calif Santa Barbara, Dept Mat, Santa Barbara, CA 93106 USA
[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
[4] Univ Calif Santa Barbara, Mitsubishi Chem Ctr Adv Mat, Santa Barbara, CA 93106 USA
[5] King Fahd Univ Petr & Minerals, Dhahran 31261, Saudi Arabia
基金
美国国家科学基金会;
关键词
CONJUGATED POLYMERS; FUSED THIOPHENES; HIGH-MOBILITY; SOLAR-CELLS; TRIPHENYLAMINE; MORPHOLOGY; FURAN;
D O I
10.1021/ma202095j
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A facile and scalable synthetic route to a soluble dithieno[3,2-b:2',3'-d]thiophene (DTT) unit has been developed, which utilizes a Stile coupling reaction to efficiently synthesize the bisthienyl sulfide intermediate. This simplifies the overall DTT synthesis to only four steps with a 44% yield and facilitates its use as a donor unit in low-band-gap polymers. Solution processable alternating D-pi-A-pi polymers (DTTBTO and DTTDPP) have been synthesized with DTT as the donor unit and either a benzothiodiazole derivative (BTO) or fused ring 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) serving as the acceptor unit. The ability to tailor the structure of these donor-acceptor systems permits a detailed understanding of structure/property relationships for band-gap engineering, absorbance, V-oc, and efficiency to be developed and applied to the design of high-performance organic solar cells.
引用
收藏
页码:9533 / 9538
页数:6
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