Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties

Fangwei Ding; Debin Xia; Xiping Ding; Ruibin Deng; Congwu Ge; Yulin Yang; Ruiqing Fan; Kaifeng Lin; Xike Gao

doi:10.1016/j.cclet.2022.02.040

Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties

Fangwei Ding
, Debin Xia^*
, Xiping Ding
, Ruibin Deng
, Congwu Ge
, Yulin Yang
, Ruiqing Fan
, Kaifeng Lin
, Xike Gao

^*Corresponding author for this work

School of Chemistry and Chemical Engineering, Harbin Institute of Technology
CAS - Shanghai Institute of Organic Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

A novel air-stable n-type benzothiaphene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current (SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.

Original language	English
Article number	107235
Journal	Chinese Chemical Letters
Volume	34
Issue number	2
DOIs	https://doi.org/10.1016/j.cclet.2022.02.040
State	Published - Feb 2023
Externally published	Yes

Keywords

Azaarenes
Deep LUMO levels
Organic semiconductor
Polycyclic aromatic hydrocarbons
n-type

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10.1016/j.cclet.2022.02.040

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title = "Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties",

abstract = "A novel air-stable n-type benzothiaphene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current (SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.",

keywords = "Azaarenes, Deep LUMO levels, Organic semiconductor, Polycyclic aromatic hydrocarbons, n-type",

author = "Fangwei Ding and Debin Xia and Xiping Ding and Ruibin Deng and Congwu Ge and Yulin Yang and Ruiqing Fan and Kaifeng Lin and Xike Gao",

note = "Publisher Copyright: {\textcopyright} 2022",

year = "2023",

month = feb,

doi = "10.1016/j.cclet.2022.02.040",

language = "英语",

volume = "34",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline

T2 - Synthesis and semiconducting properties

AU - Ding, Fangwei

AU - Xia, Debin

AU - Ding, Xiping

AU - Deng, Ruibin

AU - Ge, Congwu

AU - Yang, Yulin

AU - Fan, Ruiqing

AU - Lin, Kaifeng

AU - Gao, Xike

PY - 2023/2

Y1 - 2023/2

N2 - A novel air-stable n-type benzothiaphene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current (SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.

AB - A novel air-stable n-type benzothiaphene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current (SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.

KW - Azaarenes

KW - Deep LUMO levels

KW - Organic semiconductor

KW - Polycyclic aromatic hydrocarbons

KW - n-type

UR - https://www.scopus.com/pages/publications/85144752903

U2 - 10.1016/j.cclet.2022.02.040

DO - 10.1016/j.cclet.2022.02.040

M3 - 文章

AN - SCOPUS:85144752903

SN - 1001-8417

VL - 34

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 2

M1 - 107235

ER -

Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties

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Keywords

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