C-H-activated Csp2-Csp3 diastereoselective gridization enables ultraviolet-emitting stereo-molecular nanohydrocarbons with mulitple H···H interactions

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 () and Wei Huang ()
Additional contact information
Ying Wei: Nanjing University of Posts & Telecommunications
Chunxiao Zhong: Nanjing University of Posts & Telecommunications
Yue Sun: Nanjing University of Posts & Telecommunications
Shuwei Ma: Nanjing University of Posts & Telecommunications
Mingjian Ni: Nanjing Tech University (NanjingTech)
Xiangping Wu: Nanjing University of Posts & Telecommunications
Yongxia Yan: Nanjing University of Posts & Telecommunications
Lei Yang: Nanjing University of Posts & Telecommunications
Ilya A. Khodov: Russian Academy of Sciences
Jiaoyang Ge: Nanjing University of Posts & Telecommunications
Yang Li: Nanjing University of Posts & Telecommunications
Dongqing Lin: Nanjing University of Posts & Telecommunications
Yongxia Wang: Nanjing University of Posts & Telecommunications
Qiujing Bao: Nanjing University of Posts & Telecommunications
He Zhang: Nanjing University of Posts & Telecommunications
Shasha Wang: Nanjing University of Posts & Telecommunications
Juan Song: Nanjing University of Posts & Telecommunications
Jinyi Lin: Nanjing Tech University (NanjingTech)
Linghai Xie: Nanjing University of Posts & Telecommunications
Wei Huang: Nanjing University of Posts & Telecommunications

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: 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 (|gPL | = 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.

Date: 2024
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DOI: 10.1038/s41467-024-48130-6

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