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Molecular Orientation Change in Naphthalene Diimide Thin Films Induced by Removal of Thermally Cleavable Substituents
Chemistry of Materials ( IF 7.2 ) Pub Date : 2019-01-15 00:00:00 , DOI: 10.1021/acs.chemmater.8b05237 Tomoya Nakamura 1 , Nobutaka Shioya 1 , Takafumi Shimoaka 1 , Ryosuke Nishikubo 2 , Takeshi Hasegawa 1 , Akinori Saeki 2 , Yasujiro Murata 1 , Richard Murdey 1 , Atsushi Wakamiya 1
Chemistry of Materials ( IF 7.2 ) Pub Date : 2019-01-15 00:00:00 , DOI: 10.1021/acs.chemmater.8b05237 Tomoya Nakamura 1 , Nobutaka Shioya 1 , Takafumi Shimoaka 1 , Ryosuke Nishikubo 2 , Takeshi Hasegawa 1 , Akinori Saeki 2 , Yasujiro Murata 1 , Richard Murdey 1 , Atsushi Wakamiya 1
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The potential of naphthalene-1,8:4,5-tetracarboxylic diimide (NDI-H) as a transparent electron-transporting material was examined. A soluble precursor was designed and synthesized having two tert-butoxycarbonyl solubilizing substituents at the imide moieties. This precursor molecule, NDI-Boc, is converted to the hydrogen-substituted NDI-H by heating the spin-coated precursor films. The molecular orientation during the thermal conversion of NDI-Boc to NDI-H was examined using two-dimensional grazing incidence X-ray diffraction (2D-GIXD) and p-polarized multiple-angle incidence resolution spectrometry. It was revealed that, driven by the formation of intermolecular hydrogen bonds, the molecular orientation changes from tilted edge-on to face-on orientation. In situ 2D-GIXD measurements confirmed that the change of molecular orientation is simultaneously caused by the cleaving of the Boc substituents. Time-resolved microwave conductivity measurements were used to show that the resulting NDI-H film has anisotropic charge-carrier transport with preferential mobility in the direction perpendicular to the film plane. We fabricated perovskite solar cells to demonstrate that the NDI-H film effectively functions as the bottom electron-transporting layer in these devices.
中文翻译：
去除热裂解取代基引起的萘二酰亚胺薄膜分子取向的变化
研究了萘-1,8：4,5-四羧酸二酰亚胺（NDI-H）作为透明电子传输材料的潜力。设计并合成了具有两个叔丁基的可溶性前体-在酰亚胺部分上的-丁氧基羰基可溶取代基。通过加热旋涂的前体膜，该前体分子NDI-Boc被转化为氢取代的NDI-H。使用二维掠入射X射线衍射（2D-GIXD）和p偏振多角度入射分辨光谱法检查了NDI-Boc热转化为NDI-H期间的分子取向。结果表明，在分子间氢键形成的驱动下，分子的取向从边上的倾斜方向变为面上的倾斜方向。原位2D-GIXD测量证实，分子方向的变化是同时由Boc取代基的裂解引起的。时间分辨的微波电导率测量结果表明，所得的NDI-H薄膜具有各向异性的电荷载流子传输，且在垂直于薄膜平面的方向上具有优先的迁移率。我们制造了钙钛矿太阳能电池，以证明NDI-H膜有效地充当了这些器件中的底部电子传输层。
更新日期：2019-01-15
中文翻译：
去除热裂解取代基引起的萘二酰亚胺薄膜分子取向的变化
研究了萘-1,8：4,5-四羧酸二酰亚胺（NDI-H）作为透明电子传输材料的潜力。设计并合成了具有两个叔丁基的可溶性前体-在酰亚胺部分上的-丁氧基羰基可溶取代基。通过加热旋涂的前体膜，该前体分子NDI-Boc被转化为氢取代的NDI-H。使用二维掠入射X射线衍射（2D-GIXD）和p偏振多角度入射分辨光谱法检查了NDI-Boc热转化为NDI-H期间的分子取向。结果表明，在分子间氢键形成的驱动下，分子的取向从边上的倾斜方向变为面上的倾斜方向。原位2D-GIXD测量证实，分子方向的变化是同时由Boc取代基的裂解引起的。时间分辨的微波电导率测量结果表明，所得的NDI-H薄膜具有各向异性的电荷载流子传输，且在垂直于薄膜平面的方向上具有优先的迁移率。我们制造了钙钛矿太阳能电池，以证明NDI-H膜有效地充当了这些器件中的底部电子传输层。
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