Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors.
J Org Chem
; 81(22): 11256-11267, 2016 11 18.
Article
de En
| MEDLINE
| ID: mdl-27791365
ABSTRACT
There is a great interest in peryleneimide (PI)-containing compounds given their unique combination of good electron accepting ability, high abosorption in the visible region, and outstanding chemical, thermal, and photochemical stabilities. Thus, herein we report the synthesis of perylene imide derivatives endowed with a 1,2-diketone functionality (PIDs) as efficient intermediates to easily access peryleneimide (PI)-containing organic semiconductors with enhanced absorption cross-section for the design of tunable semiconductor organic materials. Three processable organic molecular semiconductors containing thiophene and terthiophene moieties, PITa, PITb, and PITT, have been prepared from the novel PIDs. The tendency of these semiconductors for molecular aggregation have been investigated by NMR spectroscopy and supported by quantum chemical calculations. 2D NMR experiments and theoretical calculations point to an antiparallel π-stacking interaction as the most stable conformation in the aggregates. Investigation of the optical and electrochemical properties of the materials is also reported and analyzed in combination with DFT calculations. Although the derivatives presented here show modest electron mobilities of â¼10-4 cm2V-1s-1, these preliminary studies of their performance in organic field effect transistors (OFETs) indicate the potential of these new building blocks as n-type semiconductors.
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Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
J Org Chem
Année:
2016
Type de document:
Article
Pays d'affiliation:
Espagne