Switching charge-transfer characteristics from p-type to n-type through molecular "doping" (co-crystallization)

Chemical Science
Jing ZhangQichun Zhang

Abstract

Borrowing an idea from the silicon industry, where the charge-carrier's characteristics can be changed through heteroatom implantation, we believe that the charge transport nature of organic semiconductors can be switched through molecular "doping" (co-crystallization). Here, we report a novel molecule 2,7-di-tert-butyl-10,14-di(thiophen-2-yl)phenanthro[4,5-abc][1,2,5]thiadiazolo[3,4-i]phenazine (DTPTP), which originally is a p-type (0.3 cm2 V-1 s-1) compound, and can be switched to an n-type semiconductor (DTPTP2-TCNQ, 3 × 10-3 cm2 V-1 s-1 under air conditions) through tetracyanoquinodimethane (TCNQ) doping (co-crystallization). Single crystal X-ray studies revealed that TCNQ-doped DTPTP complexes (DTPTP2-TCNQ) adopt a dense one-dimensional (1D) mixed π-π stacking mode with a ratio of DTPTP and TCNQ of 2 : 1, while pure DTPTP molecules utilize a herringbone-packing pattern. Interestingly, theoretical analysis suggested that there is a quasi-2D electron transport network in this host-guest system. Our research results might provide a new strategy, to switch the charge transport characteristics of an original system by appropriate molecular "doping" (co-crystal engineering).

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Citations

Oct 5, 2018·Chemical Society Reviews·Yu WangWenping Hu
Mar 31, 2019·Angewandte Chemie·Hui Jiang, Wenping Hu
Jan 31, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Prabhat MajumdarShinto Varghese
Feb 28, 2020·Chemical Communications : Chem Comm·Xue-Qing YangDong Wang
Nov 28, 2019·Chemistry : a European Journal·Zongrui WangQichun Zhang
Jul 7, 2020·Chemistry : a European Journal·Wei WangQichun Zhang
Nov 11, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ben-Lin Hu, Qichun Zhang
Jun 17, 2021·Chemical Reviews·Meera MadhuMahesh Hariharan
Nov 14, 2020·Small·Mohammad BodiuzzamanThalappil Pradeep
Jun 12, 2019·The Journal of Physical Chemistry Letters·Yishan WangChong-An Di
Dec 24, 2019·The Journal of Physical Chemistry Letters·Qi WeiJiansheng Jie
Jun 14, 2017·Accounts of Chemical Research·Jing ZhangDaoben Zhu
Aug 5, 2021·Nanotechnology·Arpit BhardwajPhanish Suryanarayana

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Methods Mentioned

BETA
NMR
X-ray
transmission
electron diffraction
column chromatography

Software Mentioned

SHELXL
97

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