80277-96-9

Upstream product

• 108-86-1 bromobenzene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Relevant academic research and scientific papers

Phenyl substitution in tetracene: a promising strategy to boost charge mobility in thin film transistors

Tetracene, one of the polyacene derivatives, shows eminent optical and electronic properties with relatively high stability. To take advantage of the intrinsic properties of the tetracene molecule and explore new semiconductors, herein, we report the design and synthesis of two novel p-channel tetracene derivatives, 2-(4-dodecyl-phenyl)-tetracene (C12-Ph-TET) and 2-phenyl-tetracene (Ph-TET). Top contact OTFTs were fabricated using these two materials as semiconductor layers, with charge mobilities up to 1.80 cm2 V?1 s?1 and 1.08 cm2 V?1 s?1, respectively. Our molecular modeling results indicate that the introduction of phenyl into tetracene can improve the efficient charge transport in electronic devices as a result of the increased electronic coupling between the two neighboring planes of the molecules. AFM images of the thermally evaporated thin films of these two materials show large grains, which correspond to the high mobilities of these devices. Consequently, the mobility of our OTFTs based on C12-Ph-TET is the highest for OTFTs based on tetracene derivatives reported to date. The single crystal analyses show the existence of π-π stacking interactions within the molecules with the introduction of mono-phenyl substituents, which is the main cause of the increased mobility. The impressive properties of these two materials indicate that the introduction of alkyl-phenyl and phenyl group could be an excellent method to improve the properties of the organic semiconductor materials.

Tetracene organic semiconductor material and preparation method thereof

The invention discloses a tetracene organic semiconductor material and a preparation method thereof. The structural formula of the tetracene organic semiconductor material is shown in the description; and in the formula, R is one of a C1-C40 linear or branched alkyl group, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C1-C40 halogen-substituted linear or branched alkyl group, a C2-C40 halogen-substituted alkenyl group, a C2-C40 halogen-substituted alkynyl group, an o- or m- or p-substituted 2-phenyl C1-C40 linear or branched chain substituted alkyl group, a C2-C40 linear or branched alkenyl or alkynyl group, a C1-C40 linear or branched chain substituted alkoxy group, an o- or m- or p-substituted 2-phenyl C2-C40 linear or branched alkenyl or alkynyl group, and an o- or m- or p-fluorocyclohexyl group. The method is simple, and allows a series of tetracene derivatives to be obtained. A tetracene material is modified, the mobility is improved, and foundation is provided for the application of the tetracene material.

Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes

A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1=Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2=Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2-Ar1CH2(CHO)C=C(CHO)CH2Ar2, which in many cases undergo titanium(IV) chloride-induced double Bradsher closure, providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.