Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives

Jack Ly; Kara Martin; Simil Thomas; Masataka Yamashita; Beihang Yu; Craig A. Pointer; Hiroko Yamada; Kenneth R. Carter; Sean Parkin; Lei Zhang; Jean-Luc Bredas; Elizabeth R. Young; Alejandro L. Briseno

doi:10.1021/acs.jpca.9b04203

Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives

Jack Ly, Kara Martin, Simil Thomas, Masataka Yamashita, Beihang Yu, Craig A. Pointer, Hiroko Yamada, Kenneth R. Carter, Sean Parkin, Lei Zhang, Jean-Luc Bredas, Elizabeth R. Young, Alejandro L. Briseno

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8 Scopus citations

Abstract

A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes.

Original language	English (US)
Pages (from-to)	7558-7566
Number of pages	9
Journal	Journal of Physical Chemistry A
Volume	123
Issue number	35
DOIs	https://doi.org/10.1021/acs.jpca.9b04203
State	Published - Aug 26 2019

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10.1021/acs.jpca.9b04203

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title = "Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives",

abstract = "A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes.",

author = "Jack Ly and Kara Martin and Simil Thomas and Masataka Yamashita and Beihang Yu and Pointer, {Craig A.} and Hiroko Yamada and Carter, {Kenneth R.} and Sean Parkin and Lei Zhang and Jean-Luc Bredas and Young, {Elizabeth R.} and Briseno, {Alejandro L.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: A.L.B. acknowledges the Office of Naval Research (Award N00014-16-1-2612) and the National Science Foundation (DMR-1508627). The work at Georgia Tech was supported by the Office of Naval Research (Award N00014-17-1-2208). E.R.Y. thanks the NSF Major Research Instrumentation program for funds that established the multiuser laser facility for transient absorption (CHE-1428633). K.R.C. thanks the National Science Foundation (DMR-1506968) for support. S.P. thanks the NSF MRI program for awards CHE-0319176 and CHE-1625732",

year = "2019",

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doi = "10.1021/acs.jpca.9b04203",

language = "English (US)",

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T1 - Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives

AU - Ly, Jack

AU - Martin, Kara

AU - Thomas, Simil

AU - Yamashita, Masataka

AU - Yu, Beihang

AU - Pointer, Craig A.

AU - Yamada, Hiroko

AU - Carter, Kenneth R.

AU - Parkin, Sean

AU - Zhang, Lei

AU - Bredas, Jean-Luc

AU - Young, Elizabeth R.

AU - Briseno, Alejandro L.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: A.L.B. acknowledges the Office of Naval Research (Award N00014-16-1-2612) and the National Science Foundation (DMR-1508627). The work at Georgia Tech was supported by the Office of Naval Research (Award N00014-17-1-2208). E.R.Y. thanks the NSF Major Research Instrumentation program for funds that established the multiuser laser facility for transient absorption (CHE-1428633). K.R.C. thanks the National Science Foundation (DMR-1506968) for support. S.P. thanks the NSF MRI program for awards CHE-0319176 and CHE-1625732

PY - 2019/8/26

Y1 - 2019/8/26

N2 - A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes.

AB - A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes.

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JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

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Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives

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CCDC 1960815: Experimental Crystal Structure Determination : 5,12-bis((trimethylsilyl)ethynyl)-6,11-diphenyl-5,12-epidioxytetracene dichloromethane n-hexane solvate

CCDC 1890869: Experimental Crystal Structure Determination : 5,12-bis((trimethylsilyl)ethynyl)-6,11-bis(thiophen-2-yl)-5,12-epidioxytetracene

CCDC 1960816: Experimental Crystal Structure Determination : 5,12-diphenyl-6,11-bis(phenylethynyl)tetracene

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Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives

Abstract

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Datasets

CCDC 1960815: Experimental Crystal Structure Determination : 5,12-bis((trimethylsilyl)ethynyl)-6,11-diphenyl-5,12-epidioxytetracene dichloromethane n-hexane solvate

CCDC 1890869: Experimental Crystal Structure Determination : 5,12-bis((trimethylsilyl)ethynyl)-6,11-bis(thiophen-2-yl)-5,12-epidioxytetracene

CCDC 1960816: Experimental Crystal Structure Determination : 5,12-diphenyl-6,11-bis(phenylethynyl)tetracene

Cite this