Chemistry - A European Journal p. 3566 - 3575 (2018)
Update date:2022-08-04
Topics:
Gupta, Ravindra Kumar
Shankar Rao, Doddamane S.
Prasad, S. Krishna
Achalkumar, Ammathnadu S.
Three new heteroatom bay-annulated perylene bisimides (PBIs) have been synthesized by microwave-assisted synthesis in excellent yield. N-annulated and S-annulated perylene bisimides exhibited columnar hexagonal phase, whereas Se-annulated perylene bisimide exhibited low temperature columnar oblique phase in addition to the high temperature columnar hexagonal phase. The cup shaped bay-annulated PBIs pack into columns with enhanced intermolecular interactions. In comparison to PBI, these molecules exhibited lower melting and clearing temperature, with good solubility. A small red shift in the absorption was seen in the case of N-annulated PBI, whereas S- and Se-annulated PBIs exhibited blue-shifted absorption spectra. Bay-annulation increased the HOMO and LUMO levels of the N-annulated perylene bisimide, whereas a slight increase in the LUMO level and a decrease in the HOMO levels were observed in the case of S- and Se-annulated perylene bisimides, in comparison to the simple perylene bisimide. The band gaps of PBI and PBI-N were almost same, whereas an increase in the band gaps were observed in the case of S- and Se-annulated PBIs. The tendency to freeze in the ordered glassy columnar phase for PBI-N and PBI-S will help to overcome the charge traps due to crystallization, which are detrimental to one-dimensional charge carrier mobility. These solution processable electron deficient columnar semiconductors possessing good thermal stability may form an easily accessible promising class of n-type materials.
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Doi:10.1016/j.bmcl.2004.06.029
(2004)Doi:10.1021/jo01313a051
(1980)Doi:10.1021/jo01314a054
(1980)Doi:10.1021/acscatal.6b02324
(2016)Doi:10.1021/jo01313a048
(1980)Doi:10.1002/ardp.19803130512
(1980)