Amphiphilic Self‐Assembly of an n‐Type Nanotube

Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders

“…These ligands are water soluble, as indicated by linear Lambert–Beer plots of the absorption of solutions. An exception is NDI 2 , which has been shown to aggregate in aqueous solutions at concentrations above 1.9 m m . In light of this, all of the DNA binding studies assumed a non‐aggregated state for all ligands except NDI 2 .…”

“…The CD spectra of these complexes, regardless of the type of sequence (Figure , c‐kit2 interacting with this NDI 2 ; see the Supporting Information, Figure S7, for other G‐quadruplex sequences), displayed a CD signal centred at 381 nm, which was ascribed to the NDI core. This led us to propose that this ligand is involved in a binding competition between the self‐aggregation process and the interaction with the G‐quadruplex sequences.…”

“…NDI 1 : The reaction was performed on 1 equivalent of NDA (200 mg, 0.746 mmol) and 2 equivalent of N α ‐Boc‐ l ‐lysine (367 mg, 1.491 mmol) by using the general procedure. Yield of NDI 1 : 461 mg, 85 %; 1 H NMR: δ =12.42 (br s, 2 H,), 8.63 (s, 4 H), 7.06 (d, J (H,H) =7.9 Hz, 2 H), 4.03 (4 H, t, J (H,H) =7.2 Hz), 3.86–3.79 (m, 2 H), 1.73–1.55 (br m, 8 H), 1.45–1.30 ppm (m, 22 H); 13 C NMR: δ =174.6, 163.0, 156.0, 130.8, 126.6, 126.5, 78.2, 53.7, 30.84, 28.5, 27.38.0, 23.6 ppm; FTMS‐NSI: m/z calcd for C 36 H 44 N 4 O 12 : 723.2856 [ M −H] − ; found: 723.2883.…”

“…NDI 2 : The aforementioned general procedure was followed by using NDI 1 (350 mg). Yield of NDI 2 : 332 mg, 91 %; 1 H NMR: δ =8.62 (s, 4 H), 8.27 (br s, 6 H), 4.02 (t, J (H,H) =7.3 Hz, 4 H), 3.96–3.84 (m, 2 H), 1.91–1.60 (m, 8 H), 1.57–1.29 ppm (m, 4 H); 13 C NMR: δ =171.4, 162.9, 158.8, 158.3, 130.8, 126.6, 126.4, 52.1, 50.1, 30.1, 28.9, 27.3, 24.0, 22.3 ppm; FTMS‐NSI: m/z calcd for C 30 H 30 F 6 N 4 O 12 : 733.1566 [ M −H 2 O−H] − ; found: 733.1586.…”

Rational Construction of Perylene Bisimide Columnar Superstructures with a Biased Helical Sense

“…[7] Thus, diverse chiral assemblies of functional dyes have been reported, which include hexa-peri-hexabenzocoronenes, [8,9] phthalocyanines, [10] porphyrins, [11,12] merocyanines, [13,14] oligothiophenes, [15] oligo(p-phenylenevinylene)s, [4a, 16, 17] core-substituted perylene bisimides (PBIs) [18,19] and so forth. [20,21] Several of these systems [9,12,14,17,19,21] have been shown to involve chiral amplification effect in molecular assemblies, either a "sergeants-and-soldiers" or a "majority-rules" effect. [22] However, for core-unsubstituted PBI dyes showing outstanding optical and electronic properties, [23] limited examples of chiral supramolecular assemblies have been reported, [24] and only in a few systems the detailed studies on their chiral features have been carried out.…”