34263-36-0Relevant academic research and scientific papers
Nitroaromatics as n-type organic semiconductors for field effect transistors
Ghamari, Pegah,Hamzehpoor, Ehsan,Niazi, Muhammad Rizwan,Perepichka, Dmitrii F.,Perepichka, Igor F.
supporting information, p. 6432 - 6435 (2020/06/21)
The nitro group (NO2) is one of the most common electron-withdrawing groups but it has rarely been used in the design of organic semiconductors (OSCs). Herein, we report the n-type semiconducting behavior of simple fluorenone derivatives functionalized with NO2and CN groups. While the electron mobilities measured in the thin film field-effect transistors are modest (10?6-10?4cm2V?1s?1), the nitrofluorenone OSCs offer excellent air-stability and remarkable tunability of energy levelsviafacile modification of the substitution pattern. We study the effect of substituents on the electrochemical properties, molecular and crystal structure, and the charge transport properties of nitrofluorenones to revitalize the underestimated potential of NO2functionalization in organic electronics.
Combining high electron affinity and intramolecular charge transfer in 1,3-dithiole-nitrofluorene push-pull diads
Perepichka, Dmitrii F.,Perepichka, Igor F.,Ivasenko, Oleksandr,Moore, Adrian J.,Bryce, Martin R.,Kuz'mina, Lyudmila G.,Batsanov, Andrei S.,Sokolov, Nikolai I.
experimental part, p. 2757 - 2770 (2009/04/10)
Attaching electron-rich 1,3-dithiol-2-ylidene moieties to polynitrofluorene electron acceptors leads to the formation of highly conjugated compounds 6 to 11, which combine high electron affinity with a pronounced intramolecular charge transfer (ICT) that is manifested as an intense absorption band in their visible spectra. Such a rare combination of optical and electronic properties is beneficial for several applications in optoelectronics. Thus, incorporation of fluorene-dithiole derivative 6 a into photoconductive films affords photothermoplastic storage media with dramatically increased photosensitivity in the ICT region. A wide structural variation of the dithiole and fluorene parts of the molecules reveals excellent correlation between the ICT energy and the reduction potential with the Hammett's parameters for the substituents. Although only a small solvatochromism of the ICT band was observed, heating the solution led to a pronounced blueshift, which was probably as a result of increased twisting around the C9=C14 bond that links the fluorene and dithiole moieties. X-ray crystallography analysis of 7 a, 8 a, 10 a, 11a and 13 a confirms an ICT interaction in the ground state of the molecules. The C9=C14 double bond between the donor and acceptor is substantially elongated and its length increases as the donor character of the dithiole moiety is enhanced.
