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09월 10일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능
제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내
Distinctive Substituent Effect of 2,7-Bis(
-(R)triphenylamino)pyrene on the Intramolecular Charge Transfer
2019년 8월 29일 15시 23분 42초
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10월 17일 (목요일) 11:00~12:30
, Kyung-Ryang Wee
Department of Chemistry, Daegu University, Korea
Department of Applied Chemistry, Daegu University, Korea
Intramolecular charge transfer (ICT) process in donor (D) acceptor (A) system with regards to electron push-pull substituents effect and the 2,7-position effect of pyrene were studied. These pyrene-based donor-acceptor-donor (D-A-D) compounds were prepared by palladium catalyzed Suzuki-Miyaura coupling reactions, consisting triphenylamine (TPA) as an electron donor and pyrene (pyr) units as an electron acceptor, respectively. Direct functionalization at the 2- and 7-positions of pyrene triggered the investigation into the electronic structures of 2,7-functionalized pyrene derivatives. By introducing various
-(R)-triphenylamine derivatives with electron-donating or electron-withdrawing R groups (R = CN, F, H, Me, and OMe), the energy band gaps of the D–A–D compounds were systematically controlled, and the emission colors were efficiently tuned from blue to green. In the steady state absorption spectra, all compounds exhibit a shape similar to the absorption spectrum of pyrene, which means that all compounds have pyrene properties in the ground state, due to poor π-conjugation by 2,7-position of pyrene. In addition, absorption band around 370 nm a gradual red-shift property was observed in the order of
, demonstrating that the ICT process is controlled by substituents. In particular, the emission spectra of
compound showed similar emission spectra shape of pyrene, this means that stronger the electron withdrawing group, the more pronounced the pyrene moiety properties. Except the compound
, the other compounds showed the bathochromic shift property with increasing solvent polarity, while compound
can be seen that there is little ICT process. In other words, the emission color appears to be well controlled by the substituents effect, but the
compound has little ICT process, due to the 2,7-position effect of pyrene and the strong electron withdrawing effect.
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