TY - JOUR
T1 - Switch-ON Near IR Fluorescent Dye Upon Protonation
T2 - Helically Twisted Bis(Boron Difluoride) Complex of π-Extended Corrorin
AU - Hisamune, Yutaka
AU - Kim, Taeyeon
AU - Nishimura, Keiichi
AU - Ishida, Masatoshi
AU - Toganoh, Motoki
AU - Mori, Shigeki
AU - Kim, Dongho
AU - Furuta, Hiroyuki
N1 - Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/3/26
Y1 - 2018/3/26
N2 - A novel helically twisted π-extended corrorin derivative having two boron dipyrrin (BODIPY) moieties at the periphery, a BODIPY DYEmer (6-BF2) cross-bridged with π-conjugated dipyrrinylidene unit, was synthesized and characterized. The neutral 6-BF2 is nonfluorescent due to the internal photoinduced charge transfer (CT) character in the excited state as inferred from the femtosecond transient absorption spectroscopy. However, upon protonation, the CT process is suppressed and the species H6-BF2 + becomes near infrared (IR) emissive. With the aid of rigid helical conformations in 6-BF2, the helical isomers (P- and M-forms) were resolved and their chiroptical property was investigated. The distinct circular dichroism (CD) spectral changes of the enantiomers were observed in the presence of acids, which demonstrates that 6-BF2 can be utilized for potential acid-responsive chiroptical materials.
AB - A novel helically twisted π-extended corrorin derivative having two boron dipyrrin (BODIPY) moieties at the periphery, a BODIPY DYEmer (6-BF2) cross-bridged with π-conjugated dipyrrinylidene unit, was synthesized and characterized. The neutral 6-BF2 is nonfluorescent due to the internal photoinduced charge transfer (CT) character in the excited state as inferred from the femtosecond transient absorption spectroscopy. However, upon protonation, the CT process is suppressed and the species H6-BF2 + becomes near infrared (IR) emissive. With the aid of rigid helical conformations in 6-BF2, the helical isomers (P- and M-forms) were resolved and their chiroptical property was investigated. The distinct circular dichroism (CD) spectral changes of the enantiomers were observed in the presence of acids, which demonstrates that 6-BF2 can be utilized for potential acid-responsive chiroptical materials.
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U2 - 10.1002/chem.201705516
DO - 10.1002/chem.201705516
M3 - Article
C2 - 29359822
AN - SCOPUS:85043284668
SN - 0947-6539
VL - 24
SP - 4628
EP - 4634
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 18
ER -