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@ARTICLE{Sukumaran:615367,
      author       = {Sukumaran, Divya P. and Shoyama, Kazutaka and Dubey, Rajeev
                      K. and Wuerthner, Frank},
      title        = {{C}ooperative {B}inding and {C}hirogenesis in an {E}xpanded
                      {P}erylene {B}isimide {C}yclophane},
      journal      = {Journal of the American Chemical Society},
      volume       = {146},
      number       = {31},
      issn         = {0002-7863},
      address      = {Washington, DC},
      publisher    = {ACS Publications},
      reportid     = {PUBDB-2024-06122},
      pages        = {22077-22084},
      year         = {2024},
      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.},
      cin          = {DOOR ; HAS-User},
      ddc          = {540},
      cid          = {I:(DE-H253)HAS-User-20120731},
      pnm          = {6G3 - PETRA III (DESY) (POF4-6G3) / FS-Proposal: I-20211168
                      (I-20211168) / FS-Proposal: I-20220338 (I-20220338)},
      pid          = {G:(DE-HGF)POF4-6G3 / G:(DE-H253)I-20211168 /
                      G:(DE-H253)I-20220338},
      experiment   = {EXP:(DE-H253)P-P11-20150101},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:39045838},
      UT           = {WOS:001276202900001},
      doi          = {10.1021/jacs.4c08073},
      url          = {https://bib-pubdb1.desy.de/record/615367},
}