Synthetic Approaches to Zigzag‐Shaped Oligophenylene Strands Laterally Decorated with Hydroxy Functions

Abstract

Two nanosized zigzag‐shaped oligophenylene strands incorporating 2,2′‐biphenol units were prepared by Suzuki–Miyaura coupling methodology. The two strands are made up of ten and seven phenyl rings, respectively. Two synthetic pathways were evaluated. The first involved the preparation of the target oligophenylene molecules by a sequential approach, whereas the second entailed the formation of the precursors of the target compounds in a one‐step fashion. The efficiencies of these two approaches are discussed and compared.

A Remarkable Solvent Effect on the Nuclearity of Neutral Titanium(IV)‐Based Helicate Assemblies

“…A slow diffusion of n-pentane into the resulting orange mixture led to red crystals, which were collected by filtration (yield: 76 %). [13][14][15][16][17][18][19][20][21][22][23][24][25][69][70][71]137.3,137.7,138.6,139.4,141.0,143.0,143.4,159.5,160.4,160.8,161 (4) ; a = 90, b = 105.4120 (10), g = 908; V = 27 747.1(9) (2) 3 ; T = 173(2) K; Z = 2, 1 cald = 1.166 Mg m 3 ; reflections collected = 80 349, R int = 0.0848; refinement factors: R1 = 0.1083, Rw = 0.2870, GOF = 1.100. CCDC 905356 contains the supplementary crystallographic data for this paper.…”

“…The coordination chemistry reported herein concerns the development of neutral Ti IV –helicates formed with biphenolate entities 23. Herein, we describe the ability of a tetraphenolic ligand (named LH 4 ; Figure 1),24 in which two 3‐phenyl‐2,2′‐biphenol units are connected by a para ‐phenylene spacer to react with the titanium centers. When the self‐assembly process is performed in dichloromethane followed by the diffusion of n ‐pentane, crystals of a circular trimetallic single‐strand structure (named Ti3 ) are produced exclusively.…”

A Bowl‐Shaped Circular Trinuclear Helicate Generated from a TiO4N2 Motif by a Multicomponent Self‐Assembly Approach

“…In a glass vial equipped with a screw cap was charged with LH 4 (20.8 mg, 3.47 10 À5 mol), bpym (5.5 mg, 4.110 À5 mol) and [Ti(OiPr) 4 ] (10 mL, 3.8 10 À5 mol) in dry toluene (1.5 mL). The resulting 18.5823 (7) 13.0001 (9) 17.6752 (5) c [] 25.1207 (11) 22.3624 (15) 18.1133(5) a [8] 69.4960(10) 90 66.2330(10) b [8] 84.9710 (10) 93.627(2) 81.9530(10) g [8] 69.0270 (10 mixture was heated at 100 8C in a dry bath. During the heating, orange crystals appeared in the medium.…”

“…Thus, we report the synthesis, characterization and a stability study of a neutral titanium‐based trinuclear circular helicate formed by a self‐assembly process employing three components. These components are respectively [Ti(O i Pr) 4 ], the strand LH 4 ,8 which incorporates two biphenol units linked by a para ‐phenylene bridge (Figure 1) and the 2,2′‐bipyrimidine (bpym) as a nitrogenated chelate. We also show that this set of components is well suited to generate other complex architectures constructed from a TiO 4 N 2 motif.…”

Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid

“…In addition, oligophenylenes can be used as building blocks for the synthesis of well-defined graphite subunits [13]. The conformational and electronic properties of oligophenylenes have also been subjects of intensive research [14,15,16,17,18]. Owing to such widespread interest, it is crucial to develope synthetic methods that can produce oligophenylenes with the desired chain length and connectivity pattern.…”