Synthesis Of Pentacene Research Articles

Tandem Desulfurization/C-C Coupling Reaction of Tetrathienylbenzenes on Cu(111): Synthesis of Pentacene and an Exotic Ladder Polymer.

Surface-confined reactions represent a powerful approach for the precise synthesis of low-dimensional organic materials. A complete understanding of the pathways of surface reactions would enable the rational synthesis of a wide range of molecules and polymers. Here, we report different reaction pathways of tetrathienylbenzene (T1TB) and its extended congener tetrakis(dithienyl)benzene (T2TB) on Cu(111), investigated using scanning tunneling microscopy, X-ray photoelectron spectroscopy, and density functional theory calculations. Both T1TB and T2TB undergo desulfurization when deposited on Cu(111) at room temperature. Deposition of T1TB at 453 K yields pentacene through desulfurization, hydrogen transfer, and a cascade of intramolecular cyclization. In contrast, for T2TB the intramolecular cyclization stops at anthracene and the following intermolecular C-C coupling produces a conjugated ladder polymer. We show that tandem desulfurization/C-C coupling provides a versatile approach for growing carbon-based nanostructures on metal surfaces.

ChemInform Abstract: Synthesis of Pentacene‐, Tetracene‐ and Anthracene Bisimides Using Double‐Cyclization Reaction Mediated by Bismuth(III) Triflate.

Novel bisimide-fused acenes were synthesized viabismuth triflate mediated double-cyclization reaction of acid chlorides and isocyanates. Their optical and electrical properties revealed significantly smaller HOMO–LUMO gaps compared with those of their parent acenes. Fabricated OFET based on tetracene bisimide showed n-type OFET outputs.

Synthesis of pentacene-, tetracene- and anthracene bisimides using double-cyclization reaction mediated by bismuth(iii) triflate

Novel bisimide-fused acenes were synthesized via bismuth triflate mediated double-cyclization reaction of acid chlorides and isocyanates. Their optical and electrical properties revealed significantly smaller HOMO-LUMO gaps compared with those of their parent acenes. Fabricated OFET based on tetracene bisimide showed n-type OFET outputs.