Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

Hewei Luo; Dongdong He; Yong Zhang; Shiwen Wang; Haili Gao; Ji Yan; Yang Cao; Zhengxu Cai; Luxi Tan; Shide Wu; Lizhen Wang; Zitong Liu

doi:10.1021/acs.orglett.9b03891

Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

Hewei Luo^*
, Dongdong He
, Yong Zhang
, Shiwen Wang
, Haili Gao
, Ji Yan
, Yang Cao
, Zhengxu Cai
, Luxi Tan
, Shide Wu
, Lizhen Wang
, Zitong Liu

^*Corresponding author for this work

School of Material Science and Engineering

Zhengzhou University of Light Industry
Chongqing University
CAS - Institute of Chemistry

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

16 Citations (Scopus)

Abstract

A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.

Original language	English
Pages (from-to)	9734-9737
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.9b03891
Publication status	Published - 6 Dec 2019

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10.1021/acs.orglett.9b03891

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title = "Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides",

abstract = "A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.",

author = "Hewei Luo and Dongdong He and Yong Zhang and Shiwen Wang and Haili Gao and Ji Yan and Yang Cao and Zhengxu Cai and Luxi Tan and Shide Wu and Lizhen Wang and Zitong Liu",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = dec,

day = "6",

doi = "10.1021/acs.orglett.9b03891",

language = "English",

volume = "21",

pages = "9734--9737",

journal = "Organic Letters",

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TY - JOUR

T1 - Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

AU - Luo, Hewei

AU - He, Dongdong

AU - Zhang, Yong

AU - Wang, Shiwen

AU - Gao, Haili

AU - Yan, Ji

AU - Cao, Yang

AU - Cai, Zhengxu

AU - Tan, Luxi

AU - Wu, Shide

AU - Wang, Lizhen

AU - Liu, Zitong

PY - 2019/12/6

Y1 - 2019/12/6

N2 - A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.

AB - A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.

UR - https://www.scopus.com/pages/publications/85075584868

U2 - 10.1021/acs.orglett.9b03891

DO - 10.1021/acs.orglett.9b03891

M3 - Article

C2 - 31747296

AN - SCOPUS:85075584868

SN - 1523-7060

VL - 21

SP - 9734

EP - 9737

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

Abstract

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