Aggregation-induced chirality amplification of optically active fluorescent polyurethane and a cyclic dimer in the ground and excited states

Zhiyi Song; Hiroyasu Sato; Adriana Pietropaolo; Qingyu Wang; Shuhei Shimoda; Heshuang Dai; Yoshitane Imai; Hayato Toda; Takunori Harada; Yukatsu Shichibu; Katsuaki Konishi; Masayoshi Bando; Naofumi Naga; Tamaki Nakano

doi:10.1039/d1cc05633f

Aggregation-induced chirality amplification of optically active fluorescent polyurethane and a cyclic dimer in the ground and excited states

Chem Commun (Camb). 2022 Jan 20;58(7):1029-1032. doi: 10.1039/d1cc05633f.

Authors

Affiliations

¹ Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N21W10, Kita-ku, Sapporo 001-0021, Japan. tamaki.nakano@cat.hokudai.ac.jp.
² Rigaku Corporation 4-14-4, Sendagaya, Shibuya-Ku, Tokyo 151-0051, Japan.
³ Dipartimento di Scienze della Salute, Università di Catanzaro, Catanzaro, Italy.
⁴ Technical Division, Institute for Catalysis, Hokkaido University, N21W10, Kita-ku, Sapporo 001-0021, Japan.
⁵ Graduate School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashiosaka City, Osaka 577-8502, Japan.
⁶ Department of Integrated Science and Technology, Faculty of Science and Technology, Oita University, Japan.
⁷ Faculty of Environmental Earth Science, Hokkaido University, N10, W5, Kita-ku, Sapporo 060-0810, Japan.
⁸ Department of Applied Chemistry, Shibaura Institute of Technology, College of Engineering, 3-7-5 Toyosu, Koto-ku, Tokyo 135-8548, Japan.
⁹ Integrated Research Consortium on Chemical Sciences (IRCCS), ICAT, Hokkaido University, Sapporo 001-0021, Japan.

PMID: 34951413
DOI: 10.1039/d1cc05633f

Abstract

Optically active linear polyurethane and a cyclic dimer were synthesized from 2,7-diisocyanatofluorene and 2,2'-dihydroxy-1,1'-binaphthyl. The circular dichroism (CD) spectral intensity of the polymer was amplified at a higher concentration through aggregate formation, while circularly polarized light (CPL) emission was not enhanced. The cyclic dimer's CPL emission was largely amplified (g_lum 1.1 × 10^-2) due to intermolecular excimer formation through aggregation, while the CD intensity was not affected.

MeSH terms

Circular Dichroism
Density Functional Theory
Dimerization
Fluorescent Dyes / chemistry*
Naphthols / chemistry
Polyurethanes / chemistry*
Stereoisomerism

Substances

BINOL, naphthol
Fluorescent Dyes
Naphthols
Polyurethanes