Synthesis of fluorescent fluorene-isoindole-containing mono- and oligomers

László Lázár, Miklós Nagy, Dávid Rácz, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Novel fluorene-isoindole-containing light-emitting mono- and oligomers were prepared. The synthesis of the monomers N-(4-bromo-phenyl)-2-(7-bromo-9,9- diethylfluoren-2-yl)-isoindole-1-carboxamide, N-(7-bromo-9,9-dibutylfluoren-2- yl)-2-(7-bromo-9,9-dibutylfluoren-2-yl)-isoindole-1-carboxamide, and N-[7-bromo-9,9-bis(2-ethylhexyl)-fluoren-2-yl]-2-[7-bromo-9,9-bis(2-ethylhexyl) -fluoren-2-yl]-isoindole -1-carboxamide was carried out by a three-component reaction of ortho-phthalaldehyde with the corresponding amine and isocyanide partners. The Ni(0) mediated polymerization reactions of the obtained monomers gave the corresponding mixture of oligomers from two up to twelve repeat units. The optical properties were also studied and it was found that the phenylene-containing oligomer emitted green light in dichloromethane solution, while both difluorene-containing oligomers, under the same conditions, proved to be blue light-emitters with good quantum efficiency.

Original languageEnglish
Pages (from-to)3691-3699
Number of pages9
JournalTetrahedron
Volume70
Issue number23
DOIs
Publication statusPublished - Jun 10 2014

Fingerprint

Isoindoles
Oligomers
Monomers
o-Phthalaldehyde
Methyl Green
Light
Methylene Chloride
Cyanides
Quantum efficiency
Polymerization
Amines
Optical properties
fluorene

Keywords

  • Fluorene
  • Fluorescence
  • Isocyanide
  • Isoindole
  • Light-emitting oligomer

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of fluorescent fluorene-isoindole-containing mono- and oligomers. / Lázár, László; Nagy, Miklós; Rácz, Dávid; Zsuga, M.; Kéki, S.

In: Tetrahedron, Vol. 70, No. 23, 10.06.2014, p. 3691-3699.

Research output: Contribution to journalArticle

Lázár, László ; Nagy, Miklós ; Rácz, Dávid ; Zsuga, M. ; Kéki, S. / Synthesis of fluorescent fluorene-isoindole-containing mono- and oligomers. In: Tetrahedron. 2014 ; Vol. 70, No. 23. pp. 3691-3699.
@article{338cee1d40d34afc8490389e0ceaab28,
title = "Synthesis of fluorescent fluorene-isoindole-containing mono- and oligomers",
abstract = "Novel fluorene-isoindole-containing light-emitting mono- and oligomers were prepared. The synthesis of the monomers N-(4-bromo-phenyl)-2-(7-bromo-9,9- diethylfluoren-2-yl)-isoindole-1-carboxamide, N-(7-bromo-9,9-dibutylfluoren-2- yl)-2-(7-bromo-9,9-dibutylfluoren-2-yl)-isoindole-1-carboxamide, and N-[7-bromo-9,9-bis(2-ethylhexyl)-fluoren-2-yl]-2-[7-bromo-9,9-bis(2-ethylhexyl) -fluoren-2-yl]-isoindole -1-carboxamide was carried out by a three-component reaction of ortho-phthalaldehyde with the corresponding amine and isocyanide partners. The Ni(0) mediated polymerization reactions of the obtained monomers gave the corresponding mixture of oligomers from two up to twelve repeat units. The optical properties were also studied and it was found that the phenylene-containing oligomer emitted green light in dichloromethane solution, while both difluorene-containing oligomers, under the same conditions, proved to be blue light-emitters with good quantum efficiency.",
keywords = "Fluorene, Fluorescence, Isocyanide, Isoindole, Light-emitting oligomer",
author = "L{\'a}szl{\'o} L{\'a}z{\'a}r and Mikl{\'o}s Nagy and D{\'a}vid R{\'a}cz and M. Zsuga and S. K{\'e}ki",
year = "2014",
month = "6",
day = "10",
doi = "10.1016/j.tet.2014.04.018",
language = "English",
volume = "70",
pages = "3691--3699",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "23",

}

TY - JOUR

T1 - Synthesis of fluorescent fluorene-isoindole-containing mono- and oligomers

AU - Lázár, László

AU - Nagy, Miklós

AU - Rácz, Dávid

AU - Zsuga, M.

AU - Kéki, S.

PY - 2014/6/10

Y1 - 2014/6/10

N2 - Novel fluorene-isoindole-containing light-emitting mono- and oligomers were prepared. The synthesis of the monomers N-(4-bromo-phenyl)-2-(7-bromo-9,9- diethylfluoren-2-yl)-isoindole-1-carboxamide, N-(7-bromo-9,9-dibutylfluoren-2- yl)-2-(7-bromo-9,9-dibutylfluoren-2-yl)-isoindole-1-carboxamide, and N-[7-bromo-9,9-bis(2-ethylhexyl)-fluoren-2-yl]-2-[7-bromo-9,9-bis(2-ethylhexyl) -fluoren-2-yl]-isoindole -1-carboxamide was carried out by a three-component reaction of ortho-phthalaldehyde with the corresponding amine and isocyanide partners. The Ni(0) mediated polymerization reactions of the obtained monomers gave the corresponding mixture of oligomers from two up to twelve repeat units. The optical properties were also studied and it was found that the phenylene-containing oligomer emitted green light in dichloromethane solution, while both difluorene-containing oligomers, under the same conditions, proved to be blue light-emitters with good quantum efficiency.

AB - Novel fluorene-isoindole-containing light-emitting mono- and oligomers were prepared. The synthesis of the monomers N-(4-bromo-phenyl)-2-(7-bromo-9,9- diethylfluoren-2-yl)-isoindole-1-carboxamide, N-(7-bromo-9,9-dibutylfluoren-2- yl)-2-(7-bromo-9,9-dibutylfluoren-2-yl)-isoindole-1-carboxamide, and N-[7-bromo-9,9-bis(2-ethylhexyl)-fluoren-2-yl]-2-[7-bromo-9,9-bis(2-ethylhexyl) -fluoren-2-yl]-isoindole -1-carboxamide was carried out by a three-component reaction of ortho-phthalaldehyde with the corresponding amine and isocyanide partners. The Ni(0) mediated polymerization reactions of the obtained monomers gave the corresponding mixture of oligomers from two up to twelve repeat units. The optical properties were also studied and it was found that the phenylene-containing oligomer emitted green light in dichloromethane solution, while both difluorene-containing oligomers, under the same conditions, proved to be blue light-emitters with good quantum efficiency.

KW - Fluorene

KW - Fluorescence

KW - Isocyanide

KW - Isoindole

KW - Light-emitting oligomer

UR - http://www.scopus.com/inward/record.url?scp=84899986298&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899986298&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.04.018

DO - 10.1016/j.tet.2014.04.018

M3 - Article

AN - SCOPUS:84899986298

VL - 70

SP - 3691

EP - 3699

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 23

ER -