3.7. Palladium Nanoparticles as Catalysts 888 3.8. Other Transition-Metal Complexes 888 3.9. Transition-Metal-Free Reactions 889 4. Applications 889 4.1. Alkynylation of Arenes 889 4.2. Alkynylation of Heterocycles 891 4.3. Synthesis of Enynes and Enediynes 894 4.4. Synthesis of Ynones 896 4.5. Synthesis of Carbocyclic Systems 897 4.6. Synthesis of Heterocyclic Systems 898 4.7. Synthesis of Natural Products 903 4.8. Synthesis of Electronic and Electrooptical Molecules 906

https://www.chem.ccu.edu.tw/~joyce/referance/ericyang/Chem.%20Rev/Chem.%20Rev.%202007,%20107,%20874-922.pdf

The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry†

Functionalized acenes and heteroacenes for organic electronics.

Charge-Transfer and Energy-Transfer Processes in π-Conjugated Oligomers and Polymers: A Molecular Picture

Acenes have long been the subject of intense study because of the unique electronic properties associated with their pi-bond topology. Recent reports of impressive semiconductor properties of larger homologues have reinvigorated research in this field, leading to new methods for their synthesis, functionalization, and purification, as well as for fabricating organic electronic components. Studies performed on high-purity acene single crystals revealed their intrinsic electronic properties and provide useful benchmarks for thin film device research. New approaches to add functionality were developed to improve the processability of these materials in solution. These new functionalization strategies have recently allowed the synthesis of acenes larger than pentacene, which have hitherto been largely unavailable and poorly studied, as well as investigation of their associated structure/property relationships.

The larger acenes: versatile organic semiconductors.

Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: the brick and mortar of organic electronics.

The unusual solid-state nonplanarity seen in the X-ray structures of the [N]phenylenes (an example is shown here) is shown to be most likely the result of crystal-packing-induced deformations. These conclusions are based on a study of published and eight new structure determinations, comparison with data on napththalenes and anthracenes obtained from the Cambridge Structural Database, and ab initio calculations.

On the Nature of Nonplanarity in the [N]Phenylenes

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes)†

Total syntheses of angular [7]-, [8]-, and [9]phenylene by triple cobalt-catalyzed cycloisomerization: remarkably flexible heliphenes.

In agreement with theory, the title compounds 1 and 2, which were prepared by CpCo-catalyzed cycloisomerizations of appropriate oligoalkynylbenzenes, display physical properties that are in contrast with those of the corresponding linear isomers, but that are very similar to those of the angular topomers.

A Novel Phenylene Topology: Total Syntheses of Zigzag [4]- and [5]Phenylene.

http://www.rsc.org/suppdata/cc/b5/b503173g/b503173g.pdf

Daniel Holmes

Papers

On the Nature of Nonplanarity in the [N]Phenylenes

Total Syntheses and Structures of Angular [6]- and [7]Phenylene: The First Helical Phenylenes (Heliphenes)†

Total syntheses of angular [7]-, [8]-, and [9]phenylene by triple cobalt-catalyzed cycloisomerization: remarkably flexible heliphenes.

A Novel Phenylene Topology: Total Syntheses of Zigzag [4]- and [5]Phenylene.

Hindered rotation in an “exploded” biphenyl