One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors

Jian Feng Zhao; Lin Chen; Peng Ju Sun; Xiao Ya Hou; Xiang Hua Zhao; Wei Jie Li; Ling Hai Xie; Yan Qian; Nai En Shi; Wen Yong Lai; Qu Li Fan; Wei Huang

doi:10.1016/j.tet.2010.12.065

One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors

Jian Feng Zhao, Lin Chen, Peng Ju Sun, Xiao Ya Hou, Xiang Hua Zhao, Wei Jie Li, Ling Hai Xie, Yan Qian, Nai En Shi, Wen Yong Lai, Qu Li Fan, Wei Huang

Nanjing University of Posts and Telecommunications

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

38 Scopus citations

Abstract

An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor-acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel-Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor-acceptor organic semiconductors.

Original language	English
Pages (from-to)	1977-1982
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2010.12.065
State	Published - 11 Mar 2011
Externally published	Yes

Keywords

2-Bromo-4,5-diazafluoren-9-one
Donor-acceptor
One-pot synthesis
Organic semiconductor
Tandem oxidation-bromination-rearrangement

Access to Document

10.1016/j.tet.2010.12.065

Cite this

Zhao, J. F., Chen, L., Sun, P. J., Hou, X. Y., Zhao, X. H., Li, W. J., Xie, L. H., Qian, Y., Shi, N. E., Lai, W. Y., Fan, Q. L., & Huang, W. (2011). One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors. Tetrahedron, 67(10), 1977-1982. https://doi.org/10.1016/j.tet.2010.12.065

@article{35e743943e8b419f99e98f54a3fe0e45,

title = "One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors",

abstract = "An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor-acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel-Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor-acceptor organic semiconductors.",

keywords = "2-Bromo-4,5-diazafluoren-9-one, Donor-acceptor, One-pot synthesis, Organic semiconductor, Tandem oxidation-bromination-rearrangement",

author = "Zhao, {Jian Feng} and Lin Chen and Sun, {Peng Ju} and Hou, {Xiao Ya} and Zhao, {Xiang Hua} and Li, {Wei Jie} and Xie, {Ling Hai} and Yan Qian and Shi, {Nai En} and Lai, {Wen Yong} and Fan, {Qu Li} and Wei Huang",

year = "2011",

month = mar,

day = "11",

doi = "10.1016/j.tet.2010.12.065",

language = "英语",

volume = "67",

pages = "1977--1982",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "10",

}

Zhao, JF, Chen, L, Sun, PJ, Hou, XY, Zhao, XH, Li, WJ, Xie, LH, Qian, Y, Shi, NE, Lai, WY, Fan, QL & Huang, W 2011, 'One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors', Tetrahedron, vol. 67, no. 10, pp. 1977-1982. https://doi.org/10.1016/j.tet.2010.12.065

TY - JOUR

T1 - One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors

AU - Zhao, Jian Feng

AU - Chen, Lin

AU - Sun, Peng Ju

AU - Hou, Xiao Ya

AU - Zhao, Xiang Hua

AU - Li, Wei Jie

AU - Xie, Ling Hai

AU - Qian, Yan

AU - Shi, Nai En

AU - Lai, Wen Yong

AU - Fan, Qu Li

AU - Huang, Wei

PY - 2011/3/11

Y1 - 2011/3/11

N2 - An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor-acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel-Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor-acceptor organic semiconductors.

AB - An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor-acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel-Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor-acceptor organic semiconductors.

KW - 2-Bromo-4,5-diazafluoren-9-one

KW - Donor-acceptor

KW - One-pot synthesis

KW - Organic semiconductor

KW - Tandem oxidation-bromination-rearrangement

UR - http://www.scopus.com/inward/record.url?scp=79951676579&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2010.12.065

DO - 10.1016/j.tet.2010.12.065

M3 - 文章

AN - SCOPUS:79951676579

SN - 0040-4020

VL - 67

SP - 1977

EP - 1982

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this