Journal Article

PUBDB-2024-06122

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Cooperative Binding and Chirogenesis in an Expanded Perylene Bisimide Cyclophane

Sukumaran, D. P. ; Shoyama, K.Extern* ; Dubey, R. K. ; Wuerthner, F. (Corresponding author)Extern*

2024
ACS Publications Washington, DC

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Please use a persistent id in citations: doi:10.1021/jacs.4c08073  doi:10.3204/PUBDB-2024-06122

Abstract: The encapsulation of more than one guest molecule into a synthetic cavity is a highly desirable yet a highly challenging task to achieve for neutral supramolecular hosts in organic media. Herein, we report a neutral perylene bisimide cyclophane, which has a tailored chiral cavity with an interchromophoric distance of 11.2 Å, capable of binding two aromatic guests in a π-stacked fashion. Detailed host–guest binding studies with a series of aromatic guests revealed that the encapsulation of the second guest in this cyclophane is notably more favored than the first one. Accordingly, for the encapsulation of the coronene dimer, a cooperativity factor (α) as high as 485 was observed, which is remarkably high for neutral host–guest systems. Furthermore, a successful chirality transfer, from the chiral host to encapsulated coronenes, resulted in a chiral charge-transfer (CT) complex and the rare observation of circularly polarized emission originating from the CT state for a noncovalent donor–acceptor assembly in solution. The involvement of the CT state also afforded an enhancement in the luminescence dissymmetry factor (glum) value due to its relatively large magnetic transition dipole moment. The 1:2 binding pattern and chirality-transfer were unambiguously verified by single-crystal X-ray diffraction analysis of the host–guest superstructures.

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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. FS-Proposal: I-20211168 (I-20211168) (I-20211168)
3. FS-Proposal: I-20220338 (I-20220338) (I-20220338)

Experiment(s):

1. PETRA Beamline P11 (PETRA III)

Appears in the scientific report 2024

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Database coverage:
; ; BIOSIS Previews ; Biological Abstracts ; Chemical Reactions ; Clarivate Analytics Master Journal List ; Current Contents - Life Sciences ; Current Contents - Physical, Chemical and Earth Sciences ; Ebsco Academic Search ; Essential Science Indicators ; IF >= 15 ; Index Chemicus ; JCR ; Nationallizenz ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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