Structural Refinement of Ladder-Type Perylenediimide Dimers: A Classical Tale of Conformational Dynamics was written by Myahkostupov, Mykhaylo;Prusakova, Valentina;Oblinsky, Daniel G.;Scholes, Gregory D.;Castellano, Felix N.. And the article was included in Journal of Organic Chemistry in 2013.Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone This article mentions the following:
The authors 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 mols., 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-dimensional 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 anal. characterization, and the associated methodol. is described. Also, from dynamic NMR experiments, both 1 and 2 exist in a perylene-centered conformational dynamic equilibrium (ΔG‡ = 13-17 kcal/mol), which primarily caused the observed ambiguities in conventional 1-dimensional spectra. In the experiment, the researchers used many compounds, for example, 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone).
2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem