The potential of a new series of H-bonded isoindigo (ID) based small molecules as charge transporting materials was examined. The soluble precursor units contained two terminal isoindigo units bearing tert-butoxycarbonyl (Boc) solubilizing substituents. Thiophene, thienothiophene and/or diketo pyrrolopyrrole are used as π-conjugated spacers between the isoindigo units. The protected Boc-ID units are converted to the hydrogen-substituted counterparts by annealing the spin-coated precursor films up to 220 °C. The solid state molecular ordering after Boc thermal decarboxylation was investigated using thermogravimetric analysis, UV–vis spectroscopy and X-ray diffraction analysis. The thermogravimetric analysis confirmed the full removal of Boc groups. It was revealed that the formation of terminal intermolecular hydrogen bonds gave the ability to the deprotected materials to change their molecular ordering to edge-on or face-on orientation based on the spacer size and the π-conjugated length. The [-NH----OC] H-bonding dramatically improved the strength of the intermolecular interactions and induced a significant shift on the wavelength of annealed films. The hole mobilities of isoindigo based organic materials measured by the space charge-limited current (SCLC) method and showed a tenfold improvement after thermal decarboxylation.

研究了一系列新的基于H键合的靛蓝（ID）小分子作为电荷传输材料的潜力。可溶性前体单元包含两个末端带有叔丁基的异靛蓝单元-丁氧羰基（Boc）增溶取代基。噻吩，噻吩并噻吩和/或二酮吡咯并吡咯用作异靛基单元之间的π-共轭间隔基。通过将旋涂的前体薄膜退火至最高220°C，将受保护的Boc-ID单元转化为氢取代的对应物。使用热重分析，紫外可见光谱和X射线衍射分析研究Boc热脱羧后的固态分子有序性。热重分析证实了Boc基团的完全除去。揭示了末端分子间氢键的形成赋予了脱保护的材料基于间隔物尺寸和π-共轭长度将其分子顺序改变为边缘或面对的取向的能力。[-NH ---- OC] H键可显着提高分子间相互作用的强度，并引起退火膜波长的显着变化。通过空间电荷限制电流（SCLC）方法测量的基于异靛蓝的有机材料的空穴迁移率显示出热脱羧后的十倍提高。