Journal Article

PUBDB-2023-05265

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Naphthalimide-Annulated [ n ]Helicenes: Red Circularly Polarized Light Emitters

Tian, X. ; Shoyama, K.Extern* ; Mahlmeister, B. ; Brust, F. ; Stolte, M. ; Wuerthner, F. (Corresponding author)Extern*

2023
ACS Publications Washington, DC

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Please use a persistent id in citations: doi:10.1021/jacs.3c03441  doi:10.3204/PUBDB-2023-05265

Abstract: Two [n]heliceno-bis(naphthalimides) 1 and 2 (n = 5 and 6, respectively) where two electron-accepting naphthalimide moieties are attached at both ends of helicene core were synthesized by effective two-step strategy, and their enantiomers could be resolved by chiral stationary-phase high-performance liquid chromatography (HPLC). The single-crystal X-ray diffraction analysis of enantiopure fractions of 1 and 2 confirmed their helical structure, and together with experimental and calculated circular dichroism (CD) spectra, the absolute configuration was unambiguously assigned. Both 1 and 2 exhibit high molar extinction coefficients for the $S_0–S_1$ transition and high fluorescence quantum yields (73% for 1 and 69% for 2), both being outstanding for helicene derivatives. The red circularly polarized luminescence (CPL) emission up to 615 nm for 2 with CPL brightness (BCPL) up to 66.5 M$^{–1}$ cm$^{–1}$ demonstrates its potential for applications in chiral optoelectronics. Time-dependent density functional theory (TD-DFT) calculations unambiguously showed that the large transition magnetic dipole moment |m| of 2 is responsible for its high absorbance dissymmetry $(g_{abs})$ and luminescence dissymmetry $(g_{lum})$ factor.

Note: DFG Grant WU 317/20-2, DFG Projektnummer 444286426

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Contributing Institute(s):

1. DOOR-User (DOOR ; HAS-User)

Research Program(s):

1. 6G3 - PETRA III (DESY) (POF4-6G3) (POF4-6G3)
2. DFG project 444286426 - Hybrid-Spektrometer (444286426) (444286426)

Experiment(s):

1. PETRA Beamline P11 (PETRA III)

Appears in the scientific report 2023

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Database coverage:
; ; BIOSIS Previews ; Clarivate Analytics Master Journal List ; Current Contents - Life Sciences ; Current Contents - Physical, Chemical and Earth Sciences ; Ebsco Academic Search ; IF >= 10 ; JCR ; Nationallizenz ; SCOPUS ; Web of Science Core Collection

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