Pentacene appended to a TEMPO stable free radical: The effect of magnetic exchange coupling on photoexcited pentacene

Erin T. Chernick; Rubén Casillas; Johannes Zirzlmeier; Daniel M. Gardner; Marco Gruber; Henning Kropp; Karsten Meyer; Michael R. Wasielewski; Dirk M. Guldi; Rik R. Tykwinski

doi:10.1021/ja510958k

Pentacene appended to a TEMPO stable free radical: The effect of magnetic exchange coupling on photoexcited pentacene

Erin T. Chernick, Rubén Casillas, Johannes Zirzlmeier, Daniel M. Gardner, Marco Gruber, Henning Kropp, Karsten Meyer, Michael R. Wasielewski^*, Dirk M. Guldi, Rik R. Tykwinski

^*Corresponding author for this work

Chemistry

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

59 Scopus citations

Abstract

Understanding the fundamental spin dynamics of photoexcited pentacene derivatives is important in order to maximize their potential for optoelectronic applications. Herein, we report on the synthesis of two pentacene derivatives that are functionalized with the [(2,2,6,6-tetramethylpiperidin-1-yl)oxy] (TEMPO) stable free radical. The presence of TEMPO does not quench the pentacene singlet excited state, but does quench the photoexcited triplet excited state as a function of TEMPO-to-pentacene distance. Time-resolved electron paramagnetic resonance experiments confirm that triplet quenching is accompanied by electron spin polarization transfer from the pentacene excited state to the TEMPO doublet state in the weak coupling regime.

Original language	English (US)
Pages (from-to)	857-863
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	137
Issue number	2
DOIs	https://doi.org/10.1021/ja510958k
State	Published - Jan 21 2015

ASJC Scopus subject areas

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja510958k

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title = "Pentacene appended to a TEMPO stable free radical: The effect of magnetic exchange coupling on photoexcited pentacene",

abstract = "Understanding the fundamental spin dynamics of photoexcited pentacene derivatives is important in order to maximize their potential for optoelectronic applications. Herein, we report on the synthesis of two pentacene derivatives that are functionalized with the [(2,2,6,6-tetramethylpiperidin-1-yl)oxy] (TEMPO) stable free radical. The presence of TEMPO does not quench the pentacene singlet excited state, but does quench the photoexcited triplet excited state as a function of TEMPO-to-pentacene distance. Time-resolved electron paramagnetic resonance experiments confirm that triplet quenching is accompanied by electron spin polarization transfer from the pentacene excited state to the TEMPO doublet state in the weak coupling regime.",

author = "Chernick, {Erin T.} and Rub{\'e}n Casillas and Johannes Zirzlmeier and Gardner, {Daniel M.} and Marco Gruber and Henning Kropp and Karsten Meyer and Wasielewski, {Michael R.} and Guldi, {Dirk M.} and Tykwinski, {Rik R.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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doi = "10.1021/ja510958k",

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volume = "137",

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T1 - Pentacene appended to a TEMPO stable free radical

T2 - The effect of magnetic exchange coupling on photoexcited pentacene

AU - Chernick, Erin T.

AU - Casillas, Rubén

AU - Zirzlmeier, Johannes

AU - Gardner, Daniel M.

AU - Gruber, Marco

AU - Kropp, Henning

AU - Meyer, Karsten

AU - Wasielewski, Michael R.

AU - Guldi, Dirk M.

AU - Tykwinski, Rik R.

PY - 2015/1/21

Y1 - 2015/1/21

N2 - Understanding the fundamental spin dynamics of photoexcited pentacene derivatives is important in order to maximize their potential for optoelectronic applications. Herein, we report on the synthesis of two pentacene derivatives that are functionalized with the [(2,2,6,6-tetramethylpiperidin-1-yl)oxy] (TEMPO) stable free radical. The presence of TEMPO does not quench the pentacene singlet excited state, but does quench the photoexcited triplet excited state as a function of TEMPO-to-pentacene distance. Time-resolved electron paramagnetic resonance experiments confirm that triplet quenching is accompanied by electron spin polarization transfer from the pentacene excited state to the TEMPO doublet state in the weak coupling regime.

AB - Understanding the fundamental spin dynamics of photoexcited pentacene derivatives is important in order to maximize their potential for optoelectronic applications. Herein, we report on the synthesis of two pentacene derivatives that are functionalized with the [(2,2,6,6-tetramethylpiperidin-1-yl)oxy] (TEMPO) stable free radical. The presence of TEMPO does not quench the pentacene singlet excited state, but does quench the photoexcited triplet excited state as a function of TEMPO-to-pentacene distance. Time-resolved electron paramagnetic resonance experiments confirm that triplet quenching is accompanied by electron spin polarization transfer from the pentacene excited state to the TEMPO doublet state in the weak coupling regime.

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Pentacene appended to a TEMPO stable free radical: The effect of magnetic exchange coupling on photoexcited pentacene

Abstract

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CCDC 1016831: Experimental Crystal Structure Determination

CCDC 1016830: Experimental Crystal Structure Determination

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Pentacene appended to a TEMPO stable free radical: The effect of magnetic exchange coupling on photoexcited pentacene

Abstract

ASJC Scopus subject areas

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CCDC 1016831: Experimental Crystal Structure Determination

CCDC 1016830: Experimental Crystal Structure Determination

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