Spacer-Dependent Cooperativity of Helicity in Fluorescent Bishelical Foldamers Based on L-Shaped Dibenzopyrrolo[1,2-a][1,8]naphthyridine.
chirality
cooperativity
fluorescence
foldamers
helices
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
22 Sep 2021
22 Sep 2021
Historique:
revised:
21
09
2021
received:
07
09
2021
entrez:
12
10
2021
pubmed:
13
10
2021
medline:
13
10
2021
Statut:
aheadofprint
Résumé
For the construction of helical foldamers composed of π-frameworks, the choice of appropriate π-π stacking units and π-spacers connecting them is important. The transfer of helicity between the minimal helix structural units is also an essential factor in the construction of homochiral helical foldamers. Tetramers 4 a-4 d, which have four L-shaped dibenzopyrrolo[1,2-a]naphthyridine units, were synthesized to investigate the interplay and cooperativity of the helical structures. Tetramer 4 a bridged with a biphenyl unit formed a homochiral bishelical structure with π-π stacking between the L-shaped units (3.3 Å), consisting only of (P,P)- and (M,M)-enantiomers without the (P,M)-diastereomer, owing to interplay through the axial chirality of biphenyl unit in the solid state. Similarly, in solution, thermodynamic stabilization of the two helix formations worked cooperatively to favor the bishelical form of 4 a. Furthermore, bishelical foldamer 4 a emitted intense fluorescence (Φ=0.86).
Identifiants
pubmed: 34636489
doi: 10.1002/cplu.202100407
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1421-1425Subventions
Organisme : JSPS KAKENHI
ID : JP16J08668
Organisme : JSPS KAKENHI
ID : JP20K05478
Organisme : NJRC Mater. & Dev.
Informations de copyright
© 2021 Wiley-VCH GmbH.
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Tetramer 4 a has not been successfully optically resolved due to the low helix inversion barrier of the helix unit.