Control of Circularly Polarized Luminescence by Orientation of Stacked π-Electron Systems.

[2.2]paracyclophane circularly polarized luminescence fluorophores higher-ordered structures planar chirality

Journal

Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643

Informations de publication

Date de publication:
15 May 2019
Historique:
received: 28 11 2018
revised: 07 01 2019
pubmed: 10 1 2019
medline: 10 1 2019
entrez: 10 1 2019
Statut: ppublish

Résumé

Planar chiral building blocks based on 4,7,12,15-tetrasubstituted [2.2]paracyclophanes were obtained via a synthetic route involving an optical resolution step. Planar chiral enantiomers, comprising two fluorophores that were stacked to form a V-shaped higher-ordered structure, were synthesized from these building blocks. The V-shaped molecules emitted intense circularly polarized luminescence (CPL). Their chiroptical properties were compared with those of X-shaped molecules bearing the same two fluorophores stacked together. The CPL sign of the X-shaped molecule was opposite to that of the V-shaped molecule, which is supported by the theoretical results, indicating that the CPL sign can be controlled by the orientation of the stacked fluorophores.

Identifiants

DOI: 10.1002/asia.201801741 PMID: 30623591
pubmed: 30623591
doi: 10.1002/asia.201801741
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1681-1685

Subventions

Organisme : Ministry of Education, Culture, Sports, Science and Technology
ID : 17H05165
Organisme : Ministry of Education, Culture, Sports, Science and Technology
ID : 17H05148

Informations de copyright

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Auteurs

Katsuaki Kikuchi (K)

Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.

Jun Nakamura (J)

Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.

Yuuya Nagata (Y)

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.

Hiromu Tsuchida (H)

Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.

Takahiro Kakuta (T)

Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.
WPI Nano Life Science Institute, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.

Tomoki Ogoshi (T)

Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.
WPI Nano Life Science Institute, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.

Yasuhiro Morisaki (Y)

Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
ORCID: 0000-0002-9125-2670

Classifications MeSH