Benzoselenadiazole and benzotriazole directed electrophilic C-H borylation of conjugated donor-acceptor materials

被引：24

作者：

Dash, Barada P. ^{[1
,2
]}

Hamilton, Iain ^{[3
,4
]}

Tate, Daniel J. ^{[1
]}

Crossley, Daniel L. ^{[5
]}

Kim, Ji-Seon ^{[3
,4
]}

Ingleson, Michael J. ^{[5
]}

Turner, Michael L. ^{[1
,5
]}

机构：

[1] Univ Manchester, Sch Chem, Organ Mat Innovat Ctr, Manchester M13 9PL, Lancs, England

[2] Siksha O Anusandhan Deemed Univ, Dept Chem, Bhubaneswar 751030, Odisha, India

[3] Imperial Coll London, Dept Phys, London SW7 2AZ, England

[4] Imperial Coll London, Ctr Plast Elect, London SW7 2AZ, England

[5] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF MATERIALS CHEMISTRY C | 2019年 / 7卷 / 03期

基金：

欧盟地平线“2020”; “创新英国”项目; 欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

OPTOELECTRONIC PROPERTIES; ORGANIC SEMICONDUCTORS; BAND-GAP; BENZOTHIADIAZOLE; POLYMERS; FLUORENE;

D O I：

10.1039/c8tc05131c

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

Benzoselenadiazole and benzotriazole directed electrophilic borylation using BCl3 results in the C-H functionalization of an adjacent aromatic unit and produces fused boracycles. Subsequent arylation at boron afforded air and moisture stable products displaying large bathochromic shifts and significantly reduced LUMO energy levels. OLEDs fabricated containing borylated benzoselenadiazole derivatives showed emission centered at 723 nm in the near infra-red region of the spectrum.

引用

页码：718 / 724

页数：7

共 33 条

[1] Understanding the role of ultra-thin polymeric interlayers in improving efficiency of polymer light emitting diodes [J].

Bailey, Jim ;

Wright, Edward N. ;

Wang, Xuhua ;

Walker, Alison B. ;

Bradley, Donal D. C. ;

Kim, Ji-Seon .

JOURNAL OF APPLIED PHYSICS, 2014, 115 (20)

[2] One polymer for all: benzotriazole containing donor-acceptor type polymer as a multi-purpose material [J].

Balan, Abidin ;

Baran, Derya ;

Gunbas, Gorkem ;

Durmus, Asuman ;

Ozyurt, Funda ;

Toppare, Levent .

CHEMICAL COMMUNICATIONS, 2009, (44) :6768-6770

[3] Donor-Acceptor Polymer with Benzotriazole Moiety: Enhancing the Eleetrochromic Properties of the "Donor Unit" [J].

Balan, Abidin ;

Gunbas, Gorkem ;

Durmus, Asuman ;

Toppare, Levent .

CHEMISTRY OF MATERIALS, 2008, 20 (24) :7510-7513

[4]

Baumgartner T., 2018, MAIN GROUP STRATEGIE

[5] Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications [J].

Cardona, Claudia M. ;

Li, Wei ;

Kaifer, Angel E. ;

Stockdale, David ;

Bazan, Guillermo C. .

ADVANCED MATERIALS, 2011, 23 (20) :2367-2371

[6] Near-Infrared Fluorescent Semiconducting Polymer Dots with High Brightness and Pronounced Effect of Positioning Alkyl Chains on the Comonomers [J].

Chen, Chuan-Pin ;

Huang, Ya-Chi ;

Liou, Sz-Yu ;

Wu, Pei-Jing ;

Kuo, Shih-Yu ;

Chan, Yang-Hsiang .

ACS APPLIED MATERIALS & INTERFACES, 2014, 6 (23) :21585-21595

[7] Post-polymerisation functionalisation of conjugated polymer backbones and its application in multifunctional emissive nanoparticles [J].

Creamer, Adam ;

Wood, Christopher S. ;

Howes, Philip D. ;

Casey, Abby ;

Cong, Shengyu ;

Marsh, Adam V. ;

Godin, Robert ;

Panidi, Julianna ;

Anthopoulos, Thomas D. ;

Burgess, Claire H. ;

Wu, Tingman ;

Fei, Zhuping ;

Hamilton, Iain ;

McLachlan, Martyn A. ;

Stevens, Molly M. ;

Heeney, Martin .

NATURE COMMUNICATIONS, 2018, 9

[8] Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation [J].

Crossley, D. L. ;

Cade, I. A. ;

Clark, E. R. ;

Escande, A. ;

Humphries, M. J. ;

King, S. M. ;

Vitorica-Yrezabal, I. ;

Ingleson, M. J. ;

Turner, M. L. .

CHEMICAL SCIENCE, 2015, 6 (09) :5144-5151

[9] Post-polymerization C-H Borylation of Donor-Acceptor Materials Gives Highly Efficient Solid State Near-Infrared Emitters for Near-IR-OLEDs and Effective Biological Imaging [J].

Crossley, Daniel L. ;

Urbano, Laura ;

Neumann, Robert ;

Bourke, Struan ;

Jones, Jennifer ;

Dailey, Lea Ann ;

Green, Mark ;

Humphries, Martin J. ;

King, Simon M. ;

Turner, Michael L. ;

Ingleson, Michael J. .

ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (34) :28243-28249

[10] Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials [J].

Crossley, Daniel L. ;

Vitorica-Yrezabal, Inigo ;

Humphries, Martin J. ;

Turner, Michael L. ;

Ingleson, Michael J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (35) :12439-12448

← 1 2 3 4 →