Pyrene-Fused Poly-Aromatic Regioisomers: Synthesis, Columnar Mesomorphism, and Optical Properties.
Pyrene-Fused Poly-Aromatic Regioisomers: Synthesis, Columnar Mesomorphism, and Optical Properties.
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DOI：
10.3390/molecules28041721
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发表时间：
2023-02-10
期刊：
影响因子：
4.6
通讯作者：
Donnio, Bertrand
中科院分区：
文献类型：
--
作者：
Zeng, Qing;Liu, Shuai;Lin, Hang;Zhao, Ke-Xiao;Bai, Xiao-Yan;Zhao, Ke-Qing;Hu, Ping;Wang, Bi-Qin;Donnio, Bertrand
关键词：
π-扩展芘化合物具有显着的发光和半导体特性，并且作为电致发光材料正在被广泛研究，其在有机发光二极管、晶体管和太阳能电池中的潜在用途。这里，合成了两组含芘的π-共轭多芳香族区域异构体，即2,3,10,11,14,15,20,21-八烷氧基五苯并[a,c,m,o,rst]五苯(BBPn)和2,3,6,7,13,14,17,18-八烷氧基二苯并[j,tuv]菲据报道，[9,10-b]picene (DBPn)。它们是通过 Suzuki-Miyaura 交叉偶联与 Scholl 氧化环脱氢反应分别从容易获得的前体 1,8- 和 1,6-二溴芘获得的。两组化合物都配备有8个外围脂肪链，自组装成单个六方柱状中间相，其中一个短链BBPn同系物在较低温度下也表现出另一种柱状中间相，具有矩形对称性；与 DBPn 同系物相比，BBPn 异构体还具有更宽的中间相范围和更高的中间相稳定性。这些多环芳烃都在基板上表现出强烈的正面取向倾向，并且可以通过机械剪切控制边缘对准，以实现其在光电器件中的应用。此外，BBPn和DBPn系列均显示绿黄色发光，荧光量子产率较高，约为30%。特别是，BBPn 相对于其 DBPn 异构体在吸收和发射方面均表现出蓝移现象。 DFT 结果与光学性质和中间相的稳定范围非常吻合，证实了 DBPn 的平坦度比 BBPn 的发散更大。基于这些有趣的性质，这些异构体不仅可以潜在地应用于荧光染料领域，而且还可以应用于作为电子传输材料的有机光电半导体材料领域。
π-Extended pyrene compounds possess remarkable luminescent and semiconducting properties and are being intensively investigated as electroluminescent materials for potential uses in organic light-emitting diodes, transistors, and solar cells. Here, the synthesis of two sets of pyrene-containing π-conjugated polyaromatic regioisomers, namely 2,3,10,11,14,15,20,21-octaalkyloxypentabenzo[a,c,m,o,rst]pentaphene (BBPn) and 2,3,6,7,13,14,17,18-octaalkyloxydibenzo[j,tuv]phenanthro [9,10-b]picene (DBPn), is reported. They were obtained using the Suzuki–Miyaura cross-coupling in tandem with Scholl oxidative cyclodehydrogenation reactions from the easily accessible precursors 1,8- and 1,6-dibromopyrene, respectively. Both sets of compounds, equipped with eight peripheral aliphatic chains, self-assemble into a single hexagonal columnar mesophase, with one short-chain BBPn homolog also exhibiting another columnar mesophase at a lower temperature, with a rectangular symmetry; BBPn isomers also possess wider mesophase ranges and higher mesophases’ stability than their DBPn homologs. These polycyclic aromatic hydrocarbons all show a strong tendency of face-on orientation on the substrate and could be controlled to edge-on alignment through mechanical shearing of interest for their implementation in photoelectronic devices. In addition, both series BBPn and DBPn display green-yellow luminescence, with high fluorescence quantum yields, around 30%. In particular, BBPn exhibit a blue shift phenomenon in both absorption and emission with respect to their DBPn isomers. DFT results were in good agreement with the optical properties and with the stability ranges of the mesophases by confirming the higher divergence from the flatness of DBPn compared with BBPn. Based on these interesting properties, these isomers could be potentially applied not only in the field of fluorescent dyes but also in the field of organic photoelectric semiconductor materials as electron transport materials.
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影响因子：
4.3
作者：
Girotto, Edivandro;Ferreira, Marli;Bock, Harald
通讯作者：
Bock, Harald
影响因子：
0.7
作者：
Hirose, T;Kawakami, O;Yasutake, M
通讯作者：
Yasutake, M
影响因子：
0.7
作者：
Hirose, Takuji;Shibano, Yuki;Yasutake, Mikio
通讯作者：
Yasutake, Mikio
影响因子：
2.1
作者：
Hirose, Takuji;Takai, Hiroaki;Yasutake, Mikio
通讯作者：
Yasutake, Mikio
影响因子：
8.6
作者：
ATTARD, GS;IMRIE, CT;KARASZ, FE
通讯作者：
KARASZ, FE