Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes

Yeon Ok Lee; Tuhin Pradhan; Kihang Choi; Dong Hoon Choi; Joung Hae Lee; Jong Seung Kim

doi:10.1016/j.tet.2013.05.010

Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes

Yeon Ok Lee, Tuhin Pradhan, Kihang Choi, Dong Hoon Choi, Joung Hae Lee, Jong Seung Kim

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

12 Citations (Scopus)

Abstract

The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.

Original language	English
Pages (from-to)	5908-5912
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2013.05.010
Publication status	Published - 2013 Jul 22

Bibliographical note

Funding Information:
This work was supported by the CRI project (20120000243) (J.S.K.) and Priority Research Centers Program (20120005860) of Research Institute for Natural Sciences from NRF of Korea (K.C. and D.H.C.).

Keywords

Intramolecular charge transfer (ICT)
Radical stability
Substitution N,N-dimethylamino group
Tetrakis(phenylethynyl)pyrene

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.05.010

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@article{41a43194f9894abc88ad48308da5edac,

title = "Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes",

abstract = "The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.",

keywords = "Intramolecular charge transfer (ICT), Radical stability, Substitution N,N-dimethylamino group, Tetrakis(phenylethynyl)pyrene",

author = "Lee, {Yeon Ok} and Tuhin Pradhan and Kihang Choi and Choi, {Dong Hoon} and Lee, {Joung Hae} and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the CRI project (20120000243) (J.S.K.) and Priority Research Centers Program (20120005860) of Research Institute for Natural Sciences from NRF of Korea (K.C. and D.H.C.). ",

year = "2013",

month = jul,

day = "22",

doi = "10.1016/j.tet.2013.05.010",

language = "English",

volume = "69",

pages = "5908--5912",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "29",

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TY - JOUR

T1 - Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes

AU - Lee, Yeon Ok

AU - Pradhan, Tuhin

AU - Choi, Kihang

AU - Choi, Dong Hoon

AU - Lee, Joung Hae

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the CRI project (20120000243) (J.S.K.) and Priority Research Centers Program (20120005860) of Research Institute for Natural Sciences from NRF of Korea (K.C. and D.H.C.).

PY - 2013/7/22

Y1 - 2013/7/22

N2 - The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.

AB - The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.

KW - Intramolecular charge transfer (ICT)

KW - Radical stability

KW - Substitution N,N-dimethylamino group

KW - Tetrakis(phenylethynyl)pyrene

UR - http://www.scopus.com/inward/record.url?scp=84878876162&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.05.010

DO - 10.1016/j.tet.2013.05.010

M3 - Article

AN - SCOPUS:84878876162

SN - 0040-4020

VL - 69

SP - 5908

EP - 5912

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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