TY - JOUR
T1 - Near-Infrared and Dual Emissions of Diphenylamino Group-Substituted Malachite Green Derivatives
AU - Mori, Toshiaki
AU - Sekine, Kohei
AU - Kawashima, Kyohei
AU - Mori, Toshifumi
AU - Kuninobu, Yoichiro
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Numbers JP 18H04656, 20H04824, and 21H01941, and 22H02035, Tokuyama Science Foundation, Yamada Science Foundation, and Shorai Foundation for Science and Technology, and Nanotechnology Platform Program (Molecule and Material Synthesis) of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, Grant Number JPMXP09 S-21-KU-0024. The calculations were partially performed at Research Center for Computational Science, Okazaki, Japan (Project: 21-IMS−C124 and 22-IMS−C123). We thank Assoc. Prof. Katsuhiko Fujita, Prof. Kaoru Tamada, Assoc. Prof. Yusuke Arima, Assist. Prof. Sou Ryuzaki, and Assist. Prof. Fumiyuki Toshimitsu at Kyushu University for analytical facilities.
Funding Information:
This work was supported in part by JSPS KAKENHI Grant Numbers JP 18H04656, 20H04824, and 21H01941, and 22H02035, Tokuyama Science Foundation, Yamada Science Foundation, and Shorai Foundation for Science and Technology, and Nanotechnology Platform Program (Molecule and Material Synthesis) of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, Grant Number JPMXP09 S‐21‐KU‐0024. The calculations were partially performed at Research Center for Computational Science, Okazaki, Japan (Project: 21‐IMS−C124 and 22‐IMS−C123). We thank Assoc. Prof. Katsuhiko Fujita, Prof. Kaoru Tamada, Assoc. Prof. Yusuke Arima, Assist. Prof. Sou Ryuzaki, and Assist. Prof. Fumiyuki Toshimitsu at Kyushu University for analytical facilities.
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022/8/19
Y1 - 2022/8/19
N2 - Novel triarylmethanols and triarylmethyl cations with diphenylamino groups were designed and synthesized. The triarylmethyl cations exhibited near-infrared (NIR) emission in toluene solution, solid film state, and polystyrene (PS) film. The emission intensities of the triarylmethyl cations were strongest in the PS film. The relative quantum yield of the PS film increased as the number of diphenylamino groups increased. In addition, triarylmethanols exhibit dual emission in their aggregated state owing to the intermolecular interactions between triphenyl amine moieties and/or hydroxy groups. These findings are interesting because NIR and dual emissions are not observed in the dimethylamino group-substituted triarylmethyl cation, which is referred to as the “malachite green,” and the corresponding triarylmethanol, respectively.
AB - Novel triarylmethanols and triarylmethyl cations with diphenylamino groups were designed and synthesized. The triarylmethyl cations exhibited near-infrared (NIR) emission in toluene solution, solid film state, and polystyrene (PS) film. The emission intensities of the triarylmethyl cations were strongest in the PS film. The relative quantum yield of the PS film increased as the number of diphenylamino groups increased. In addition, triarylmethanols exhibit dual emission in their aggregated state owing to the intermolecular interactions between triphenyl amine moieties and/or hydroxy groups. These findings are interesting because NIR and dual emissions are not observed in the dimethylamino group-substituted triarylmethyl cation, which is referred to as the “malachite green,” and the corresponding triarylmethanol, respectively.
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U2 - 10.1002/ejoc.202200873
DO - 10.1002/ejoc.202200873
M3 - Article
AN - SCOPUS:85136962436
SN - 1434-193X
VL - 2022
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 31
M1 - e202200873
ER -