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@ARTICLE{Mahlmeister:593234,
author = {Mahlmeister, Bernhard and Schembri, Tim and Stepanenko,
Vladimir and Shoyama, Kazutaka and Stolte, Matthias and
Wuerthner, Frank},
title = {{E}nantiopure {J}-{A}ggregate of {Q}uaterrylene {B}isimides
for {S}trong {C}hiroptical {NIR}-{R}esponse},
journal = {Journal of the American Chemical Society},
volume = {145},
number = {24},
issn = {0002-7863},
address = {Washington, DC},
publisher = {ACS Publications},
reportid = {PUBDB-2023-05334},
pages = {13302 - 13311},
year = {2023},
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.},
cin = {DOOR ; HAS-User},
ddc = {540},
cid = {I:(DE-H253)HAS-User-20120731},
pnm = {6G3 - PETRA III (DESY) (POF4-6G3) / DFG project 444286426 -
Hybrid-Spektrometer (444286426)},
pid = {G:(DE-HGF)POF4-6G3 / G:(GEPRIS)444286426},
experiment = {EXP:(DE-H253)P-P11-20150101},
typ = {PUB:(DE-HGF)16},
pubmed = {37285519},
UT = {WOS:001008513400001},
doi = {10.1021/jacs.3c03367},
url = {https://bib-pubdb1.desy.de/record/593234},
}