Pi-Extended Diindole-Fused Azapentacenone: Synthesis, Characterization, and Photophysical and Lithium-Storage Properties

Jianfeng Zhao; Renping Li; Wei Ai; Dai Dong; Jiewei Li; Lin Chen; Linghai Xie; Ting Yu; Wei Huang

doi:10.1002/asia.201501366

Pi-Extended Diindole-Fused Azapentacenone: Synthesis, Characterization, and Photophysical and Lithium-Storage Properties

Chem Asian J. 2016 May 6;11(9):1382-7. doi: 10.1002/asia.201501366. Epub 2016 Jan 21.

Authors

Jianfeng Zhao^{1

2}, Renping Li¹, Wei Ai³, Dai Dong¹, Jiewei Li¹, Lin Chen⁴, Linghai Xie⁵, Ting Yu⁶, Wei Huang^{7

8}

Affiliations

¹ Key Laboratory of Flexible Electronics (KLOFE) and, Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center, for Advanced Materials (SICAM), Nanjing Tech University (NanjingTech), 30 South Puzhu Road, Nanjing, 211816, P.R. China.
² Key Laboratory for Organic Electronics and, Information Displays (KLOEID) and Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing, 210023, P.R. China.
³ Division of Physics and Applied Physics, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371, Singapore.
⁴ Nanjing Polytechnic Institute, Nanjing, 210048, P.R. China.
⁵ Key Laboratory for Organic Electronics and, Information Displays (KLOEID) and Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing, 210023, P.R. China. iamlhxie@njupt.edu.cn.
⁶ Division of Physics and Applied Physics, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371, Singapore. yuting@ntu.edu.sg.
⁷ Key Laboratory of Flexible Electronics (KLOFE) and, Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center, for Advanced Materials (SICAM), Nanjing Tech University (NanjingTech), 30 South Puzhu Road, Nanjing, 211816, P.R. China. iamwhuang@njtech.edu.cn.
⁸ Key Laboratory for Organic Electronics and, Information Displays (KLOEID) and Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing, 210023, P.R. China. iamwhuang@njtech.edu.cn.

PMID: 26717256
DOI: 10.1002/asia.201501366

Abstract

Pi-extended polyaromatics tend to exhibit improved electronic properties with respect to the intrinsic structures. Herein, the rational design of a π-extended diindole-fused diazapentacenone (IP), with a nine-ring-fused core, obtained by applying an intramolecular Friedel-Crafts diacylation synthetic routine, is reported. The chemical structure, physical properties, and morphology of IP were fully characterized. Serving as an organic cathode material for a lithium-ion battery, the as-prepared nanorods of π-extended IP display higher conductivity and superior electrochemical performance than those of the naked diazapentacenone without diindole fusion.

Keywords: charge transfer; conjugation; electrochemistry; lithium; polyaromatics.

Publication types

Research Support, Non-U.S. Gov't