Journal Article

PUBDB-2026-00914

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Self‐assembled Helical Tetramer Stack of Terrylene Bisimide in Solution and Crystalline State

Soldner, S. ; Shoyama, K.Extern* ; Stolte, M. ; Wuerthner, F. (Corresponding author)Extern*

2026
Wiley-VCH Weinheim

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Please use a persistent id in citations: doi:10.1002/anie.2434302  doi:10.3204/PUBDB-2026-00914

Abstract: A terrylene bisimide (TBI) derivative $\bf1$ bearing bulky meta-terphenyl imide substituents is shown to self-assemble into helical $\bf{[1_4]}$ tetramer stacks in solution. Driven by strong dispersion and electrostatic forces, a direct transition from monomers into defined tetramers is already observed in the micromolar concentration range (∼10$^{−6}$ M) in methylcyclohexane at room temperature, corresponding to a π–π-interaction strength of ΔG = −40.1 kJ mol$^{−1}$ for the respective π–π-stacking interaction between two neighboring TBIs. Upon addition of perylene ($\bf{P}$), a further growth of the stacks toward $\bf{[P.1_4.P]}$ hexalayers is observed where the guest molecules are stacked at the peripheral positions. In contrast, upon addition of the larger coronene ($\bf{C}$), the equilibrium shifts toward 1:2 complexes $\bf{[C.1.C]}$ where each TBI is surrounded by two coronene neighbors. Single crystal X-ray analyses of the pristine $\bf{[1_4]}$ tetramer stack as well as the $\bf{[P.1_4.P]}$ hexalayer stack and the 1:2 trilayer $\bf{[C.1.C]}$ unambiguously confirm the unique stacking arrangements.

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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 G:(GEPRIS)444286426 - Hybrid-Spektrometer (444286426) (444286426)
3. FS-Proposal: I-20220939 (I-20220939) (I-20220939)
4. FS-Proposal: I-20230262 (I-20230262) (I-20230262)

Experiment(s):

1. PETRA Beamline P11 (PETRA III)

Appears in the scientific report 2026

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Database coverage:
; ; ; Chemical Reactions ; Clarivate Analytics Master Journal List ; Current Contents - Life Sciences ; Current Contents - Physical, Chemical and Earth Sciences ; DEAL Wiley ; 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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