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

Chemistry

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

18 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
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 - Sep 5 2019

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Funding

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.

Funders	Funder number
National Science Foundation (NSF)	CHE-0319176, CHE-1428633, CHE-1625732, N00014-17-1-2208, DMR-1506968, DMR-1508627
Office of Naval Research	N00014-16-1-2612

ASJC Scopus subject areas

Physical and Theoretical Chemistry

Access to Document

10.1021/acs.jpca.9b04203

Cite this

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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 Bredas, \{Jean Luc\} and Young, \{Elizabeth R.\} and Briseno, \{Alejandro L.\}",

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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.

PY - 2019/9/5

Y1 - 2019/9/5

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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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JF - Journal of Physical Chemistry A

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

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