Unknown

Dataset Information

0

π-Extended Rubrenes via Dearomative Annulative π-Extension Reaction.


ABSTRACT: Among a large variety of organic semiconducting materials, rubrene (5,6,11,12-tetraphenyltetracene) represents one of the most prominent molecular entities mainly because of its unusually high carrier mobility. Toward finding superior rubrene-based organic semiconductors, several synthetic strategies for related molecules have been established. However, despite its outstanding properties and significant attention in the field of materials science, late-stage functionalizations of rubrene remains undeveloped, thereby limiting the accessible chemical space of rubrene-based materials. Herein, we report on a late-stage π-extension of rubrene by dearomative annulative π-extension (DAPEX), leading to the generation of rubrene derivatives having an extended acene core. The Diels-Alder reaction of rubrene with 4-methyl-1,2,4-triazoline-3,5-dione occurred to give 1:1 and 1:2 cycloadducts which further underwent iron-catalyzed annulative diarylation. The thus-formed 1:1 and 1:2 adducts were subjected to radical-mediated oxidation and thermal cycloreversion to furnish one-side and two-side π-extended rubrenes, respectively. These π-extended rubrenes displayed a marked red shift in absorption and emission spectra, clearly showing that the acene π-system of rubrene was extended not only structurally but also electronically. The X-ray crystallographic analysis uncovered interesting packing modes of these π-extended rubrenes. Particularly, two-side π-extended rubrene adopts a brick-wall packing structure with largely overlapping two-dimensional face-to-face π-π interactions. Finally, organic field-effect transistor devices using two-side π-extended rubrene were fabricated, and their carrier mobilities were measured. The observed maximum hole mobility of 1.49 × 10-3 cm2V-1 s-1, which is a comparable value to that of the thin-film transistor using rubrene, clearly shows the potential utility of two-side π-extended rubrene in organic electronics.

SUBMITTER: Matsuoka W 

PROVIDER: S-EPMC9837837 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

altmetric image

Publications

π-Extended Rubrenes via Dearomative Annulative π-Extension Reaction.

Matsuoka Wataru W   Kawahara Kou P KP   Ito Hideto H   Sarlah David D   Itami Kenichiro K  

Journal of the American Chemical Society 20221223 1


Among a large variety of organic semiconducting materials, rubrene (5,6,11,12-tetraphenyltetracene) represents one of the most prominent molecular entities mainly because of its unusually high carrier mobility. Toward finding superior rubrene-based organic semiconductors, several synthetic strategies for related molecules have been established. However, despite its outstanding properties and significant attention in the field of materials science, late-stage functionalizations of rubrene remains  ...[more]

Similar Datasets

| S-EPMC8225822 | biostudies-literature
| S-EPMC11290328 | biostudies-literature
| S-EPMC8162369 | biostudies-literature
| S-EPMC4339889 | biostudies-literature
| S-EPMC9132060 | biostudies-literature
| S-EPMC6180308 | biostudies-literature
| S-EPMC9299636 | biostudies-literature
| S-EPMC7463262 | biostudies-literature
| S-EPMC11584004 | biostudies-literature