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• W2318182919 endingPage "8644" @default.
• W2318182919 startingPage "8634" @default.
• W2318182919 abstract "We have synthesized and thoroughly characterized two representative ladder-type acetylene-bridged perylenediimide dimers bearing long alkyl chain solubilizing groups, bis[1-ethynyl-N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] ([PDICC]2, 1) and 1,1′-ethynyl-bis[N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] ([PDI]2CC, 2). In these dimeric PDI molecules, NMR-based structural characterization became nontrivial because severe 1H spectral broadening and greater than expected numbers of observed 13C resonances substantially complicated the interpretation of traditional 1-D spectra. However, rational two-dimensional NMR approaches based on both homo- and heteronuclear couplings (1H–1H COSY; 1H–13C HSQC), in conjunction with high-level structural DFT calculations (GIAO/B3LYP/6-31G(d,p)/PCM, chloroform), were readily applied to these structures, producing well-defined analytical characterization, and the associated methodology is described in detail. Furthermore, on the basis of dynamic NMR experiments, both 1 and 2 were found to exist in a perylene-centered conformational dynamic equilibrium (ΔG‡ = 13–17 kcal/mol), which primarily caused the observed ambiguities in conventional 1-D spectra." @default.
• W2318182919 created "2016-06-24" @default.
• W2318182919 creator A5005270265 @default.
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• W2318182919 creator A5029838157 @default.
• W2318182919 creator A5087982679 @default.
• W2318182919 date "2013-08-23" @default.
• W2318182919 modified "2023-09-23" @default.
• W2318182919 title "Structural Refinement of Ladder-Type Perylenediimide Dimers: A Classical Tale of Conformational Dynamics" @default.
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• W2318182919 doi "https://doi.org/10.1021/jo401348w" @default.
• W2318182919 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23941640" @default.
• W2318182919 hasPublicationYear "2013" @default.
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