期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 13, 期 18, 页码 2619-2625出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800631
关键词
fluorescence; liquid crystals; stimuli-responsive materials; structure-activity relationships; sulfur heterocycles
资金
- JSPS KAKENHI program of the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT) [2401, JP25102540, JP15H00764, 18K055263]
- Shorai Foundation for Science and Technology
- Oil & Fat Industry Kaikan
- Murata Science Foundation
- Next Generation Leading Research Fund for 2017 of the Kagawa University Research Promotion Program (KURPP)
- Izumi Science and Technology Foundation
- Tokyo Kasei Chemical Promotion Foundation
We have designed and synthesized two room-temperature-fluorescent pi-conjugated liquids based on the N-heteroacene framework (1 and 2). These two a-conjugated liquids, which contained one and two thiophene rings, respectively, exhibited different electronic properties and rheology behaviors. Single-crystal X-ray analysis of dithiophene-appended compound 4 revealed that two thiophene rings hindered the interactions of the imino N atoms with acids through the formation of interactions between the S atoms of the thiophene rings and the imino N atoms of the pyrazine group. On the other hand, monothiophene-appended molecules 1 and 3 each contained an unhindered imino N atom on the opposite site to the thiophene ring. Upon dissolving various acids with different pK(a) values in compounds 1 and 2, these slight structural differences gave rise to marked differences in their acid-response behaviors, thereby resulting in the emission of variously colored fluorescence in the liquid state. Furthermore, when acids with lower pK(a) values was dissolved in compounds 1 and 2, phase transition occurred from an isotropic liquid state to a self-organized liquid-crystalline phase.
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