Journal Article

PUBDB-2023-05334

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Enantiopure J-Aggregate of Quaterrylene Bisimides for Strong Chiroptical NIR-Response

Mahlmeister, B. ; Schembri, T. ; Stepanenko, V. ; Shoyama, K.Extern* ; 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.3c03367  doi:10.3204/PUBDB-2023-05334

Abstract: Chiral polycyclic aromatic hydrocarbons can be tailored for next-generation photonic materials by carefully designing their molecular as well as supramolecular architectures. Hence, excitonic coupling can boost the chiroptical response in extended aggregates but is still challenging to achieve by pure self-assembly. Whereas most reports on these potential materials cover the UV and visible spectral range, systems in the near infrared (NIR) are underdeveloped. We report a new quaterrylene bisimide derivative with a conformationally stable twisted π-backbone enabled by the sterical congestion of a fourfold bay-arylation. Rendering the π-subplanes accessible by small imide substituents allows for a slip-stacked chiral arrangement by kinetic self-assembly in low polarity solvents. The well dispersed solid-state aggregate reveals a sharp optical signature of strong J-type excitonic coupling in both absorption (897 nm) and emission (912 nm) far in the NIR region and reaches absorption dissymmetry factors up to 1.1 × 10$^{–2}$. The structural elucidation was achieved by atomic force microscopy and single-crystal X-ray analysis which we combined to derive a structural model of a fourfold stranded enantiopure superhelix. We could deduce that the role of phenyl substituents is not only granting stable axial chirality but also guiding the chromophore into a chiral supramolecular arrangement needed for strong excitonic chirality.

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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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