C–H Bond Transformations Leading to the Synthesis of Organic Functional Materials

Abstract

In this review, transition-metal-catalyzed or-mediated C-H transformations leading to the synthesis of organic functional materials, such as oligomers, polymers, and π-conjugated molecules, are summarized. 1 Introduction 2 Oligomers and Polymers 2.1 Synthesis of Oligomers and Polymers 2.2 Chemical Modification of Polymers 3 π-Conjugated Molecules 3.1 Indenes and Fluorenes 3.2 Acenes 3.3 Triphenylenes 3.4 Chemical Modification of Perylene Diimides 3.5 Nanographenes 3.6 Condensed Polycyclic π-Conjugated Molecules with Five-Membered Heteroaromatic Rings 3.7 π-Conjugated Molecules with Nitrogen-Containing Six-Membered Heteroaromatics 3.8 Porphyrins 3.9 Miscellaneous (π-Conjugated Molecules) 4 Miscellaneous (Excluding Polymers and π-Conjugated Molecules) 5 Outlook and Conclusions

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

“…The authors confirmed the electrophilic nature of the active oxidizing species. The latter demonstrated high 3˝/2˝ratios (40)(41)(42)(43)(44)(45)(46)(47)(48)(49), alcohol/ketone ratios > 5, and high stereospecificity in the oxidation of cis-1,2-dimethylcyclohexane [187]; kinetic studies revealed a sizable kinetic isotopic effect (k H /k D 4.5-4.7), indicating that that the H atom lies on the reaction coordinate and participates in the C-H bond breaking step. Altogether, the experimental data provided indirect evidence in favor of the participation of a high-valent (presumably oxometal(V) [188]) species, ruling out the contribution of a free-radical-driven oxidation pathway.…”

Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives

“…The UV-vis spectra of 7aa, 7bb, and 7ba were measured in chloroform, and the normalized UV-vis spectra are shown in Figure 1. These compounds showed similar peak patterns between 300 and 500 nm, and the π-π* transitions (p-band) for 7aa, 7bb, and 7ba were observed at 426 nm [11]. The peaks corresponding to n-π* transitions (α-band) were observed at 456-469 nm and were red-shifted with growing intensity as the number of hexyloxy groups increases.…”

“…However, in search of more efficient synthetic routes, C-H arylation reactions have been increasingly utilized in recent years for the rapid expansion of the aromatic frameworks [10][11][12][13][14][15].…”

The Development of Novel C-H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules

“…Recently, some such reactions have been reported, and there have been several reviews, 24 including our own, 25 of such topics. In this section, I focus on the synthesis of π conjugated molecules bearing heteroatom(s) or a Lewis acid base interaction and on polymers.…”