Non-classical control of solid-state aggregation-induced enhanced circularly polarized luminescence in chiral perylene diimides. Issue 21 (24th May 2019)

• Record Type: Journal Article
• Authors: Watanabe, Kouhei; Taniguchi, Ayano; Kaji, Daiki; Hara, Nobuyuki; Hosoya, Tomomasa; Kanesaka, Aoba; Harada, Takunori; Nishikawa, Hiroyuki; Imai, Yoshitane
• Is Part Of: Tetrahedron. Volume 75:Issue 21(2019)
• Page Start: 2944
• Page End: 2948
• Publication Date: 2019-05-24
• Subjects: Aggregation-induced-enhancement -- Chirality -- Circular dichroism -- Luminescence -- Perylene; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.025
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Organic fluorescent molecules are gaining importance because of their potential applications in many devices. Optically active N, N′ -bis((1 R )-1-naphthylethyl)perylene-3, 4, 9, 10-tetracarboxylic diimide [( R, R )-1-BNP ] and N, N′- bis((1 R )-2-naphthylethyl)perylene-3, 4, 9, 10-tetracarboxylic diimide [( R, R )-2-BNP ] and their antipode, [( S, S )-1-BNP and ( S, S )-2-BNP ], emit aggregation-induced enhanced (AIEnh) circularly polarized luminescence (CPL) on both a solid organic polymer film (poly(methyl methacrylate)) and solid inorganic KBr pellet. An opposite chirality is essential for generating CPL of inverted sign. However, a pair of enantiomeric organic molecules may not always be easy to prepare. Interestingly, the chiral perylene fluorophores synthesized in this study can emit both positive and negative AIEnh-CPL in the solid state, depending on their position on the naphthylene groups. In addition, no CPL was observed in these compounds from their dilute solutions. Graphical abstract: Image 1 Highlights: Optically active N, N′- bis((1 R )-1-naphthylethyl)perylene-3, 4, 9, 10-tetracarboxylic diimide [( R, R )-1-BNP ] and N, N′- bis((1 R )-2-naphthylethyl)perylene-3, 4, 9, 10-tetracarboxylic diimide [( R, R )-2-BNP ] and their antipode, [( S, S )-1-BNP and ( S, S )-2-BNP ] were successfully prepared. These chiral perylene diimides could emit aggregation-induced enhanced (AIEnh) circularly polarized luminescence (CPL) on both a solid organic polymer film (poly(methyl methacrylate)) and solid inorganic KBr pellet. Chiral bis-naphthylethylperylene diimides can emit both positive and negative AIEnh-CPL in the solid state, depending on their position on the naphthylene groups.