Facile transformation of 1-aryltriphenylenes into dibenzo[fg,op]tetracenes by intramolecular Scholl cyclodehydrogenation: synthesis, self-assembly, and charge carrier mobility of large π-extended discogens
Facile transformation of 1-aryltriphenylenes into dibenzo[fg,op]tetracenes by intramolecular Scholl cyclodehydrogenation: synthesis, self-assembly, and charge carrier mobility of large π-extended discogens
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通过分子内 Scholl 环脱氢将 1-芳基三亚苯轻松转化为二苯并[fg,op]并四苯：大 δ 扩展 disogens 的合成、自组装和载流子迁移率
DOI：
10.1039/c6tc04530h
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发表时间：
2017-01
影响因子：
6.4
通讯作者：
B Donnio
中科院分区：
文献类型：
--
作者：
B Q Wang;H Monobe;B Heinrich;B Donnio
寻找具有增强的电荷传输特性和自组织能力的新型有机半导体在有机电子学新兴领域的新应用开发中起着关键作用。我们以六取代苯并菲为原料合成了两个系列的双嵌段介晶材料，包括（i）1-芳基-2，3，6，7，10，11-六取代苯并菲（戊氧基）三苯（14种新化合物）通过适当的1-溴苯并菲前体和各种芳基硼酸之间的Suzuki交叉偶联反应和（ii）不对称的面二苯并[fg，[op]并四苯通过FeCl_3-氧化环化脱氢反应，合成了11个新化合物。通过偏光显微镜、差示扫描显微镜和小角X射线散射研究了介晶性。大多数芳基取代的苯并菲衍生物表现出单一的六边形柱状中间相，在小的温度范围内各向异性或单向异性，这种低稳定性可能归因于自由旋转的大体积侧芳烃基团，其破坏了完美的堆叠。相应的更刚性和平坦的二苯并[fg，op]并四苯衍生物也自组织成六方柱状中间相，但具有比它们的亲本更大的中间相稳定性，并且在略高于室温下发生。测定了其紫外维斯吸收光谱和荧光发射光谱。在溶液中，四苯比芳基苯并菲显示出更强的光致发光，而在薄膜中观察到相反的情况，其中观察到一种极性1-芳基苯并菲的强激基缔合物发射。用飞行时间光电流技术测量了两种典型盘状体的载流子迁移率。结果表明，具有侧核偶极的盘状体在中间相中显示出10−4 cm 2 V−1 s−1的空穴迁移率，而非极性化合物在其亚稳诱导有序相中显示出10−2 cm 2 V−1 s−1的空穴迁移率。载流子迁移率作为超分子组织的功能进行了讨论。
The search for new organic semiconductors with enhanced charge transport properties and self-organizing abilities plays a pivotal role in the development of new applications in the emerging field of organic electronics. We have synthesized two series of discotic mesogenic materials derived from hexasubstituted triphenylene, including (i) 1-aryl-2,3,6,7,10,11-hexakis(pentyloxy)triphenylenes (14 new compounds) by a Suzuki cross-coupling reaction between the appropriate 1-bromotriphenylene precursor and various arylboronic acids and (ii) unsymmetrical facial dibenzo[fg,op]tetracene discotic molecules (11 new compounds) by an FeCl3-oxidized cyclodehydrogenation reaction of the former. The mesomorphism has been investigated by polarizing optical microscopy, differential scanning microscopy, and small-angle X-ray scattering. Most aryl-substituted triphenylene derivatives exhibit a single hexagonal columnar mesophase, enantiotropic over small temperature ranges or monotropic, with this low stability being likely attributed to the free-rotating bulky side-on arene group that disrupts a perfect stacking. The corresponding more rigid and flat dibenzo[fg,op]tetracene derivatives also self-organize into a hexagonal columnar mesophase, but with a larger mesophase stability than their parents, and occurring slightly above room temperature. The UV/vis absorption and fluorescence emission spectra have been measured. Tetracenes show stronger photoluminescence than aryltriphenylene in solution, while the reversed is observed in thin films, where a strong excimer emission for one of the polar 1-aryltriphenylenes is observed. The charge carrier mobility of two representative discogens has been measured by the time-of-flight photocurrent technique. The results show that the discogen with a lateral nucleus dipole displays a hole mobility of 10−4 cm2 V−1 s−1 in the mesophase, while the non-polar compound exhibits a hole mobility of 10−2 cm2 V−1 s−1 in its metastable-induced ordered phase. The charge carrier mobility is discussed as a function of the supramolecular organization.
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影响因子：
3.3
作者：
A. Ochse;A. Kettner;J. Kopitzke;J. Wendorff;H. Bässler
通讯作者：
A. Ochse;A. Kettner;J. Kopitzke;J. Wendorff;H. Bässler
影响因子：
4.9
作者：
K. Zhao;Chao Chen;H. Monobe;P. Hu;Bin-Qin Wang;Y. Shimizu
通讯作者：
K. Zhao;Chao Chen;H. Monobe;P. Hu;Bin-Qin Wang;Y. Shimizu
影响因子：
3.3
作者：
Bassam Alameddine;Olivier F. Aebischer;B. Heinrich;D. Guillon;B. Donnio;T. Jenny
通讯作者：
Bassam Alameddine;Olivier F. Aebischer;B. Heinrich;D. Guillon;B. Donnio;T. Jenny
影响因子：
5.2
作者：
Qing T. Zhang;P. Prins;S. C. Jones;S. Barlow;T. Kondo;Zesheng An;L. Siebbeles;S. Marder
通讯作者：
Qing T. Zhang;P. Prins;S. C. Jones;S. Barlow;T. Kondo;Zesheng An;L. Siebbeles;S. Marder
影响因子：
--
作者：
K. Zhao;Ling-Ling An-Ling;Xiao-Bo Zhang;Wenhao Yu;P. Hu;Bi-qin Wang;Jing Xu;Q. Zeng;H. Monobe;Y. Shimizu;B. Heinrich;B. Donnio
通讯作者：
K. Zhao;Ling-Ling An-Ling;Xiao-Bo Zhang;Wenhao Yu;P. Hu;Bi-qin Wang;Jing Xu;Q. Zeng;H. Monobe;Y. Shimizu;B. Heinrich;B. Donnio