N-Annulated indenofluorene (NIF), a structural isomer of the well-known N-annulated perylene (NP), has been synthesized. While the band gap of NP is larger than that of perylene, the band gap of NIF (1.40 eV) is smaller than that of parent indeno2,1-cfluorene (1.60 eV) due to the inclusion of a nearly planar 8π azepine ring in the π-conjugated backbone, enhancing the core antiaromaticity. The ground state properties are evaluated by structural (single-crystal) and spectral (NMR, UV-vis-NIR, and CV) analyses and supported by computations (NICS and ring current). NIF is an ambipolar material with good electron mobility (1.58 × 10-3 cm2 V-1 s-1) and high hole mobility (1.79 × 10-2 cm2 V-1 s-1), surpassing the hole mobility of the unipolar NP isomer.
Saha et al. (Thu,) studied this question.
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