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Lee, Junghoon,Jang, Moonjeong,Lee, Sang Myeon,Yoo, Dohyuk,Shin, Tae Joo,Oh, Joon Hak,Yang, Changduk American Chemical Society 2014 ACS APPLIED MATERIALS & INTERFACES Vol.6 No.22
<P>Over the past few years, one of the most remarkable advances in the field of polymer solar cells (PSCs) has been the development of fluorinated 2,1,3-benzothiadiazole (BT)-based polymers that lack the solid working principles of previous designs, but boost the power conversion efficiency. To assess a rich data set for the influence of the fluorinated BT units on the charge-transport characteristics in organic field-effect transistors (OFETs), we synthesized two new polymers (<B>PDPP-FBT</B> and <B>PDPP-2FBT</B>) incorporating diketopyrrolopyrrole (DPP) and either single- or double-fluorinated BT and thoroughly investigated them via a range of techniques. Unlike the small differences in the absorption properties of <B>PDPP-FBT</B> and its nonfluorinated analogue (<B>PDPP-BT</B>), the introduction of doubly fluorinated BT into the polymer backbone induces a noticeable change in its optical profiles and energy levels, which results in a slightly wider bandgap and deeper HOMO for <B>PDPP-2FBT</B>, relative to the others. Grazing incidence X-ray diffraction (GIXD) analysis reveals that both fluorinated polymer films have long-range orders along the out-of-plane direction, and π–π stacking in the in-plane direction, implying semicrystalline lamellar structures with edge-on orientations in the solid state. Thanks to the strong intermolecular interactions and highly electron-deficient π-systems driven by the inclusion of F atoms, the polymers exhibit electron mobilities of up to 0.42 and 0.30 cm<SUP>2</SUP> V<SUP>–1</SUP> s<SUP>–1</SUP> for <B>PDPP-FBT</B> and <B>PDPP-2FBT</B>, respectively, while maintaining hole mobilities higher than 0.1 cm<SUP>2</SUP> V<SUP>–1</SUP> s<SUP>–1</SUP>. Our results highlight that the use of fluorinated BT blocks in the polymers is a promising molecular design strategy for improving electron transporting performance without sacrificing their original hole mobility values.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/aamick/2014/aamick.2014.6.issue-22/am505925w/production/images/medium/am-2014-05925w_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/am505925w'>ACS Electronic Supporting Info</A></P>
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Siloxane‐Based Hybrid Semiconducting Polymers Prepared by Fluoride‐Mediated Suzuki Polymerization
Lee, Junghoon,Han, A‐,Reum,Lee, Sang Myeon,Yoo, Dohyuk,Oh, Joon Hak,Yang, Changduk WILEY‐VCH Verlag 2015 Angewandte Chemie Vol.127 No.15
<P><B>Abstract</B></P><P>Siloxane‐containing materials are a large and important class of organic‐inorganic hybrids. In this report, a practical variation of the Suzuki polymerization to generate semiconducting polymeric hybrids based on siloxane units, which proceeds under essentially nonbasic conditions, is presented. This method generates solution‐processable poly(diketopyrrolopyrrole‐<I>alt</I>‐benzothiadiazole) (PDPPBT‐Si) consisting of the hybrid siloxane substituents, which could not be made using conventional methods. PDPPBT‐Si exhibits excellent ambipolar transistor performance with well‐balanced hole and electron FET mobilities. The siloxane‐containing DPP‐thiophene polymer classes (PDPP3T‐Si and PDPP4T‐Si), synthesized by this method, exhibit high hole mobility of up to 1.29 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP>. This synthetic approach should provide access to a variety of novel siloxane‐containing conjugated semiconductor classes by using a variety of aryldihalides and aryldiboronic acids/esters.</P>
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