Enantiopure Dinaphtho[2,3-b:2,3-f]thieno[3,2-b]thiophenes : reaching high magnetoresistance effect in OFETs

Volpi, Martina and Jouclas, Rémy and Liu, Jie and Liu, Guangfeng and Catalano, Luca and McIntosh, Nemo and Bardini, Marco and Gatsios, Christos and Modesti, Federico and Turetta, Nicholas and Beljonne, David and Cornil, Jérôme and Kennedy, Alan R. and Koch, Norbert and Erk, Peter and Samorì, Paolo and Schweicher, Guillaume and Geerts, Yves H. (2023) Enantiopure Dinaphtho[2,3-b:2,3-f]thieno[3,2-b]thiophenes : reaching high magnetoresistance effect in OFETs. Advanced Science, 10 (26). 2301914. ISSN 2198-3844 (https://doi.org/10.1002/advs.202301914)

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Chiral molecules are known to behave as spin filters due to the chiral induced spin selectivity (CISS) effect. Chirality can be implemented in molecular semiconductors in order to study the role of the CISS effect in charge transport and to find new materials for spintronic applications. In this study, the design and synthesis of a new class of enantiopure chiral organic semiconductors based on the well-known dinaphtho[2,3-b:2,3-f]thieno[3,2-b]thiophene (DNTT) core functionalized with chiral alkyl side chains is presented. When introduced in an organic field-effect transistor (OFET) with magnetic contacts, the two enantiomers, (R)-DNTT and (S)-DNTT, show an opposite behavior with respect to the relative direction of the magnetization of the contacts, oriented by an external magnetic field. Each enantiomer displays an unexpectedly high magnetoresistance over one preferred orientation of the spin current injected from the magnetic contacts. The result is the first reported OFET in which the current can be switched on and off upon inversion of the direction of the applied external magnetic field. This work contributes to the general understanding of the CISS effect and opens new avenues for the introduction of organic materials in spintronic devices.