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Diazulenorubicene as a Non-benzenoid Isomer of peri-Tetracene with Two Sets of 5/7/5 Membered Rings Showing Good Semiconducting Properties.
Qin, Liyuan; Huang, Yan-Ying; Wu, Botao; Pan, Jinliang; Yang, Junfang; Zhang, Jing; Han, Guangchao; Yang, Suyu; Chen, Liangliang; Yin, Zheng; Shu, Yilin; Jiang, Lang; Yi, Yuanping; Peng, Qian; Zhou, Xiong; Li, Cheng; Zhang, Guanxin; Zhang, Xi-Sha; Wu, Kai; Zhang, Deqing.
Afiliación
  • Qin L; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Huang YY; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Wu B; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Pan J; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Yang J; College of Chemistry and Molecular Engineering, Peking University, 100871, Beijing, China.
  • Zhang J; College of Chemistry and Molecular Engineering, Peking University, 100871, Beijing, China.
  • Han G; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Yang S; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Chen L; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Yin Z; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Shu Y; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Jiang L; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Yi Y; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Peng Q; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Zhou X; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Li C; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Zhang G; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
  • Zhang XS; School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, Beijing, China.
  • Wu K; College of Chemistry and Molecular Engineering, Peking University, 100871, Beijing, China.
  • Zhang D; Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, CAS Center of Excellence in Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China.
Angew Chem Int Ed Engl ; 62(39): e202304632, 2023 Sep 25.
Article en En | MEDLINE | ID: mdl-37338996
ABSTRACT
Non-benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non-benzenoid isomer of peri-tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non-aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR-TMS) shows p-type semiconducting properties with a hole mobility up to 1.27 cm2  V-1 s-1 . Moreover, further extension to larger non-benzenoid PAHs with 19 rings was achieved through on-surface chemistry from the DAR derivative with one alkynyl group.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China