Controlling the Macroscopic Chirality of Organic Materials Based on 1,3,5‐Trialkynylbenzenes

Abstract

By changing the position of the homochiral alkoxy substituents of C3‐symmetric 1,3,5‐trialkynylbenzenes from the center to the periphery, the macroscopic chirality of the resulting aggregates (crystals or fibers), studied by various spectroscopic and microscopic techniques, was inverted, as confirmed by single‐crystal X‐ray diffraction analysis.

“Concentration-in-Control” self-assembly concept at the liquid–solid interface challenged

“… 16 Moreover, an increased π-system promotes π–π stacking interactions between molecules in solution. 25 Indeed, such compounds having extended π-conjugation are known to form nanoscale molecular stacks in solution. However, their formation is solvent specific.…”

Nonlinear Optical Thin Film Device from a Chiral Octopolar Phenylacetylene Liquid Crystal

“…From 1,3,5-triiodo-2,4,6-tridecyloxybenzene and 1-[( S )-2-methylbutyloxy]-4-ethynylbenzene, pure 6 is obtained as yellow oil after column chromatography (50:1 hex–Et 2 O) in 12% yield (73 mg). 1 H NMR (300 MHz, CDCl 3 ) δ 8.04 (d, J = 8.2 Hz, 6 H), 7.58 (d, J = 8.2 Hz, 6 H), 4.38 (t, J = 6.2 Hz, 6 H), 4.11–4.27 (m, 9 H), 1.93–1.82 (m, 9 H), 1.62–1.48 (m, 12 H), 1.33–1.18 (m, 12 H), 1.03 (d, J = 6.7 Hz, 9 H), 0.97 (t, J = 7.4 Hz, 9 H), 0.86 (t, J = 6.4 Hz, 9 H); 13 C NMR (125 MHz, CDCl 3 ) δ 166.0, 163.7, 131.1, 130.0, 129.5, 128.0, 107.7, 96.5, 84.4, 75.0, 69.7, 65.8, 34.3, 31.8, 30.6, 29.6, 29.5, 29.3, 26.3, 26.2, 22.6, 16.5, 15.2, 14.1, 11.3; MALDI-HRMS: calcd for C 78 H 108 O 9 + Na 1211.7886, found 1211.7884.…”

Synthesis of Multiarmed Thienylene–Tetrafluorophenylene Alternating Copolymers under Transition-Metal-Free Conditions

“…3-Trimethylsilyl-1-propanol (2.58 g, 19.5 mmol) was added to sodium hydride (0.84 g, 35 mmol) at room temperature. After the mixure was stirred for 30 min, 1,3,5-trifluoro-2,4,6-triiodobenzene (2.80 g, 5.49 mmol) was added to the mixture followed by addition of 1,3-dimethyl-2-imidazolidinone (DMI, 5 mL). The mixture was stirred at 45 °C overnight.…”