New fused conjugated molecules with fused thiophene and pyran units for organic electronic materials

Abstract

Fused conjugated molecules TTCTTC and TTTCTTTC with up to ten heterocycles were constructed by fusing fused-thiophene to the chromeno[6,5,4-def]chromene unit.

Novel Synthetic Approach to Heteroatom Doped Polycyclic Aromatic Hydrocarbons: Optimizing the Bottom-Up Approach to Atomically Precise Doped Nanographenes

“…Two interesting compounds containing thiophene and pyran units were described. The synthesis ( Scheme 41 ) starts from 1,5-dibromo-4,8-dimethoxynaphthalene ( 184 ), which was converted into the correspondent organo-zinc derivative [ 108 ]. Its Negishi coupling with the proper reagent and the subsequent demethylation followed by the CuI catalyzed cyclization gave the expected compounds 187 and 189 .…”

Towards the Bisbenzothienocarbazole Core: A Route of Sulfurated Carbazole Derivatives with Assorted Optoelectronic Properties and Applications

“…The inclusion of heterocycles into the pentacene backbone has been a frequently exploited strategy in the search for novel materials with enhanced stability and performance. Notably, many derivatives containing or combining thiophene, pyrrole or even more extended cores such as [1]benzothieno [3,2-b] [1]benzothiophene (BTBT) have achieved this goal [15][16][17][18][19][20]. Carbazole as a synthetic building block also represents an important source of organic molecules with assorted applications within the optoelectronic field.…”

O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- to Seven-Membered Rings

“…Compared to the five- or six-membered N- or S-containing heteroaromatics, O-based extended π-systems are less common, with 7-membered rings being very rare, i.e., oxepin, and five-membered furans the most popular rings. The two main synthetic approaches include intramolecular carbon–heteroatom bond formation of biaryl alcohols and intramolecular C–C bond formation of biaryl ethers . As depicted in Scheme , the preparation of five- and six-membered O-annulated PAHs were successfully reported through, for example, base-promoted cyclization of o -ethynylphenol substructures, acid-mediated cyclization of alkynes with alcohols or ketones, acid-mediated condensation between ketones and phenols, Friedel–Crafts reactions (followed by cyclodehydrogenation), Claisen condensation between arylaldehydes and naphthols (followed by oxidation), cross-condensation between hydroquinone and arylaldehyde derivatives for the simultaneous formation of C–C and C–O bonds, and Rh-catalyzed C–H activation/annulations of arylaldehydes with diaryl alkynes .…”