C-H-activated Csp 2-Csp 3 diastereoselective gridization enables ultraviolet-emitting stereo-molecular nanohydrocarbons with mulitple H···H interactions
oleh: Ying Wei, Chunxiao Zhong, Yue Sun, Shuwei Ma, Mingjian Ni, Xiangping Wu, Yongxia Yan, Lei Yang, Ilya A. Khodov, Jiaoyang Ge, Yang Li, Dongqing Lin, Yongxia Wang, Qiujing Bao, He Zhang, Shasha Wang, Juan Song, Jinyi Lin, Linghai Xie, Wei Huang
| Format: | Article |
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| Diterbitkan: | Nature Portfolio 2024-06-01 |
Deskripsi
Abstract Gridization is an emerging molecular integration technology that enables the creation of multifunctional organic semiconductors through precise linkages. While Friedel-Crafts gridization of fluorenols is potent, direct linkage among fluorene molecules poses a challenge. Herein, we report an achiral Pd-PPh3-cataylized diastereoselective (>99:1 d.r.) gridization based on the C-H-activation of fluorene to give dimeric and trimeric windmill-type nanogrids (DWGs and TWGs). These non-conjugated stereo-nanogrids showcase intramolecular multiple H…H interactions with a low field shift to 8.51 ppm and circularly polarized luminescence with high luminescent dissymmetry factors (|g PL | = 0.012). Significantly, the nondoped organic light-emitting diodes (OLEDs) utilizing cis-trans-TWG1 emitter present an ultraviolet electroluminescent peak at ~386 nm (CIE: 0.17, 0.04) with a maximum external quantum efficiency of 4.17%, marking the highest record among nondoped ultraviolet OLEDs based on hydrocarbon compounds and the pioneering ultraviolet OLEDs based on macrocycles. These nanohydrocarbon offer potential nanoscafflolds for ultraviolet light-emitting optoelectronic applications.