Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.
Identifieur interne : 000024 ( Main/Exploration ); précédent : 000023; suivant : 000025Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.
Auteurs : Ryoichi Ishimatsu [Japon] ; Tomohiko Edura [Japon] ; Chihaya Adachi [Japon] ; Koji Nakano [Japon] ; Toshihiko Imato [Japon]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) ; 2016.
Abstract
The photophysical properties and electrogenerated chemiluminescence (ECL) of three donor-acceptor molecules composed of dicyanobenzene and methyl-, tert-butyl-, and phenyl-substituted carbazolyl groups, 1,2,3,5-tetrakis(3,6-disubstituted-carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN-Me, 4CzIPN-tBu, and 4CzIPN-Ph, respectively) are described. These molecules show delayed fluorescence as a result of thermal spin upconversion from the lowest triplet state to the lowest singlet state at room temperature. The three molecules showed yellow to yellowish-red ECL. Remarkably, the ECL efficiencies of 4CzIPN-tBu in dichloromethane reached almost 40 %. Moreover, stable ECL was emitted from 4CzIPN-tBu and 4CzIPN-Ph. In case of 4CzIPN-Me, the ECL intensity decreased during voltage cycles because of polymerization. Quantum chemical calculations revealed that polymerization was inhibited by the steric hindrance of the bulky tert-butyl and phenyl groups on the carbazolyl moieties and lowered the spin density on the carbazolyl groups through electron conjugation for 4CzIPN-Ph.
DOI: 10.1002/chem.201600077
PubMed: 26916843
Affiliations:
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first="Tomohiko" last="Edura">Tomohiko Edura</name><affiliation wicri:level="1"><nlm:affiliation>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395</wicri:regionArea><wicri:noRegion>819-0395</wicri:noRegion></affiliation></author><author><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name><affiliation wicri:level="1"><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, 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Japan. imato@cstf.kyushu-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395</wicri:regionArea><wicri:noRegion>819-0395</wicri:noRegion></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="e-ISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The photophysical properties and electrogenerated chemiluminescence (ECL) of three donor-acceptor molecules composed of dicyanobenzene and methyl-, tert-butyl-, and phenyl-substituted carbazolyl groups, 1,2,3,5-tetrakis(3,6-disubstituted-carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN-Me, 4CzIPN-tBu, and 4CzIPN-Ph, respectively) are described. These molecules show delayed fluorescence as a result of thermal spin upconversion from the lowest triplet state to the lowest singlet state at room temperature. The three molecules showed yellow to yellowish-red ECL. Remarkably, the ECL efficiencies of 4CzIPN-tBu in dichloromethane reached almost 40 %. Moreover, stable ECL was emitted from 4CzIPN-tBu and 4CzIPN-Ph. In case of 4CzIPN-Me, the ECL intensity decreased during voltage cycles because of polymerization. Quantum chemical calculations revealed that polymerization was inhibited by the steric hindrance of the bulky tert-butyl and phenyl groups on the carbazolyl moieties and lowered the spin density on the carbazolyl groups through electron conjugation for 4CzIPN-Ph.</div></front></TEI><affiliations><list><country><li>Japon</li></country></list><tree><country name="Japon"><noRegion><name sortKey="Ishimatsu, Ryoichi" sort="Ishimatsu, Ryoichi" uniqKey="Ishimatsu R" first="Ryoichi" last="Ishimatsu">Ryoichi Ishimatsu</name></noRegion><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name><name sortKey="Edura, Tomohiko" sort="Edura, Tomohiko" uniqKey="Edura T" first="Tomohiko" last="Edura">Tomohiko Edura</name><name sortKey="Imato, Toshihiko" sort="Imato, Toshihiko" uniqKey="Imato T" first="Toshihiko" last="Imato">Toshihiko Imato</name><name sortKey="Nakano, Koji" sort="Nakano, Koji" uniqKey="Nakano K" first="Koji" last="Nakano">Koji Nakano</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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