Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 6, Pages 3132-3143Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00084
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Funding
- MEXT, Japan [JP15K05415, JP15K05416]
- Kurata Memorial Hitachi Science and Technology Foundation
- Cooperative Research Program of Network Joint Research Center for Materials and Devices (Osaka University) [2015396]
- Cooperative Research Program of Network Joint Research Center for Materials and Devices (Kyushu University) [2015474]
- Grants-in-Aid for Scientific Research [26288098, 15K05415, 15K05416] Funding Source: KAKEN
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pi-Extended thiadiazoloquinoxaline (TQ) derivatives 1a,b-3a,b, in which a tetraalkoxyphenanthrene moiety is annulated with the TQ core and benzene rings are incorporated via the ethynylene spacer, were synthesized. They display absorption bands reaching into 750 nm and possess the electron-affinity comparable to [60]fullerene. The CF3- and OMe-substituents on the benzene rings have moderate effects on modulation of the HOMO and LUMO levels. Tetraalkoxyphenanthrene-fused TQs 1a,b-3a,b aggregate in the solid state and assemble in solution through pi-pi stacking interactions. The self-assembly of 1a,b-3a,b into 1D superstructures was confirmed, and the difference in the alkoxy groups and the solvents for self-assembly proved to change their morphology. Comparison of the properties of 1a and those of reference compounds 4 and 5 clarified the effects of both the fusion of the phenanthrene moiety and the introduction of ethynylene spacers on the properties.
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