Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles

G.S. Pilzak; S. Fratiloiu; J. Baggerman; F.C. Grozema; E.J.R. Sudhölter; L.D.A. Siebbeles; H. Zuilhof

doi:10.1021/jp903081p

Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles

G.S. Pilzak, S. Fratiloiu, J. Baggerman, F.C. Grozema, E.J.R. Sudhölter, L.D.A. Siebbeles, H. Zuilhof

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

2 Citations (Scopus)

Abstract

High yields of the radical cations of oligodiacetylenes have been prepared by photoinduced electron transfer using a positively charged cosensitizer and by pulse radiolysis. The absorption maxima of the oligodiacetylene (ODA) radical cations show a bathochromic shift to the infrared region and a large increase of their lifetimes with chain elongation. Their reactivity toward nucleophiles decreases for longer ODAs, illustrating clearly the stabilizing effect of charge delocalization along the oligomeric chain. This also implies a very low reactivity of ODA radical cations toward trace amounts of water in optoelectronic devices.

Original language	English
Pages (from-to)	11095-11100
Journal	The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
Volume	113
Issue number	32
DOIs	https://doi.org/10.1021/jp903081p
Publication status	Published - 2009

Keywords

density-functional theory
optoelectronic properties
electronic-structure
pulse-radiolysis
exchange-energy
liquid benzene
polydiacetylene
model
ion
oligo(phenylenevinylene)s

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10.1021/jp903081p

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Pilzak, G. S., Fratiloiu, S., Baggerman, J., Grozema, F. C., Sudhölter, E. J. R., Siebbeles, L. D. A., & Zuilhof, H. (2009). Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles. The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical, 113(32), 11095-11100. https://doi.org/10.1021/jp903081p

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title = "Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles",

abstract = "High yields of the radical cations of oligodiacetylenes have been prepared by photoinduced electron transfer using a positively charged cosensitizer and by pulse radiolysis. The absorption maxima of the oligodiacetylene (ODA) radical cations show a bathochromic shift to the infrared region and a large increase of their lifetimes with chain elongation. Their reactivity toward nucleophiles decreases for longer ODAs, illustrating clearly the stabilizing effect of charge delocalization along the oligomeric chain. This also implies a very low reactivity of ODA radical cations toward trace amounts of water in optoelectronic devices.",

keywords = "density-functional theory, optoelectronic properties, electronic-structure, pulse-radiolysis, exchange-energy, liquid benzene, polydiacetylene, model, ion, oligo(phenylenevinylene)s",

author = "G.S. Pilzak and S. Fratiloiu and J. Baggerman and F.C. Grozema and E.J.R. Sudh{\"o}lter and L.D.A. Siebbeles and H. Zuilhof",

year = "2009",

doi = "10.1021/jp903081p",

language = "English",

volume = "113",

pages = "11095--11100",

journal = "The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical",

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Pilzak, GS, Fratiloiu, S, Baggerman, J, Grozema, FC, Sudhölter, EJR, Siebbeles, LDA & Zuilhof, H 2009, 'Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles', The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical, vol. 113, no. 32, pp. 11095-11100. https://doi.org/10.1021/jp903081p

Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles. / Pilzak, G.S.; Fratiloiu, S.; Baggerman, J. et al.
In: The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical, Vol. 113, No. 32, 2009, p. 11095-11100.

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

TY - JOUR

T1 - Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles

AU - Pilzak, G.S.

AU - Fratiloiu, S.

AU - Baggerman, J.

AU - Grozema, F.C.

AU - Sudhölter, E.J.R.

AU - Siebbeles, L.D.A.

AU - Zuilhof, H.

PY - 2009

Y1 - 2009

N2 - High yields of the radical cations of oligodiacetylenes have been prepared by photoinduced electron transfer using a positively charged cosensitizer and by pulse radiolysis. The absorption maxima of the oligodiacetylene (ODA) radical cations show a bathochromic shift to the infrared region and a large increase of their lifetimes with chain elongation. Their reactivity toward nucleophiles decreases for longer ODAs, illustrating clearly the stabilizing effect of charge delocalization along the oligomeric chain. This also implies a very low reactivity of ODA radical cations toward trace amounts of water in optoelectronic devices.

AB - High yields of the radical cations of oligodiacetylenes have been prepared by photoinduced electron transfer using a positively charged cosensitizer and by pulse radiolysis. The absorption maxima of the oligodiacetylene (ODA) radical cations show a bathochromic shift to the infrared region and a large increase of their lifetimes with chain elongation. Their reactivity toward nucleophiles decreases for longer ODAs, illustrating clearly the stabilizing effect of charge delocalization along the oligomeric chain. This also implies a very low reactivity of ODA radical cations toward trace amounts of water in optoelectronic devices.

KW - density-functional theory

KW - optoelectronic properties

KW - electronic-structure

KW - pulse-radiolysis

KW - exchange-energy

KW - liquid benzene

KW - polydiacetylene

KW - model

KW - ion

KW - oligo(phenylenevinylene)s

U2 - 10.1021/jp903081p

DO - 10.1021/jp903081p

M3 - Article

SN - 1520-6106

VL - 113

SP - 11095

EP - 11100

JO - The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical

JF - The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical

IS - 32

ER -

Radical Cations of All-Trans Oligodiacetylenes: Optical Absorption and Reactivity toward Nucleophiles

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Keywords

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