Abstract
The influence of backbone fluorination and sidechain regiochemistry on an indacendithiophene (IDT) core containing electron withdrawing N-cyanoimine groups is investigated.
Highlights
Conjugated organic semiconductors (OSCs) are one of the key enabling materials for the predicted generation of printed electronic devices.[1,2] Extensive research effort has resulted in the development of a number of promising solution processable materials
The results indicated that the structure is planar in all three isomers, suggesting that unlike dicyanomethylene, N-cyanoimine would not introduce any undesired steric interactions with the fluorinated core
Introduction of the N-cyanoimine groups was confirmed to be effective at stabilising the lowest unoccupied molecular orbital (LUMO) (À4.16 eV to À4.19 eV)
Summary
Conjugated organic semiconductors (OSCs) are one of the key enabling materials for the predicted generation of printed electronic devices.[1,2] Extensive research effort has resulted in the development of a number of promising solution processable materials. This is usually expressed in terms of the energy level of the lowest unoccupied molecular orbital (LUMO), which should be sufficiently low-lying to enable charge injection from common electrode materials. This is typically achieved by the functionalization of an aromatic core with a number of strongly electron withdrawing groups, like nitriles, carbonyl, (di)imide and halogens.[9,11,12,13,14] Low lying LUMO levels can help to improve the ambient stability of the resulting reduced species.[15,16,17,18] In addition to energetic considerations, it is important for charge transport that the material has a high degree of solid-state ordering with a strong electronic coupling between adjacent units.[19,20,21,22]
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