TY - JOUR
T1 - N-Confused Phlorin-Prodigiosin Chimera
T2 - meso-Aryl Oxidation and π-Extension Triggered by Peripheral Coordination
AU - Su, Guangxian
AU - Li, Qizhao
AU - Ishida, Masatoshi
AU - Li, Chengjie
AU - Sha, Feng
AU - Wu, Xin Yan
AU - Wang, Lu
AU - Baryshnikov, Glib
AU - Li, Dawei
AU - Ågren, Hans
AU - Furuta, Hiroyuki
AU - Xie, Yongshu
N1 - Funding Information:
This work at ECUST was financially supported by the Shanghai Municipal Science and Technology Major Project (Grant No.2018SHZDZX03) and the international cooperation program of Shanghai Science and Technology Committee (17520750100), NSFC (21971063, 21772041, 21702062, 21811530005), and the Program of Introducing Talents of Discipline to Universities (B160170). The work at Kyushu University was supported by Grants-in-Aid for Scientific Research (JP19K05439 and JP19H04586) from the Japan Society for the Promotion of Science (JSPS) and the Tokuyama Science Foundation. The authors thank Research Center of Analysis and Test of East China University of Science and Technology for the help on the characterization.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/1/20
Y1 - 2020/1/20
N2 - An N-confused phlorin isomer bearing a dipyrrin moiety at the α-position of the confused pyrrole ring (1) was synthesized. PdII and BIII coordination at the peripheral prodigiosin-like moiety of 1 afforded the corresponding complexes 2 and 3. Reflux of 2 in triethylamine (TEA) converted the meso-phenyl into the PdII-coordinating phenoxy group to afford 4. Under the same reaction conditions, TEA was linked to the α-position of the dipyrrin unit in 3 as an N,N-diethylaminovinyl group to afford 5. Furthermore, peripheral coordination of BIII in 3 and 5 improved the planarity of the phlorin macrocycle and thus facilitated the coordination of AgIII at the inner cavity to afford 3-Ag and 5-Ag, respectively. These results provide an effective approach for developing unique porphyrinoids through peripheral coordination.
AB - An N-confused phlorin isomer bearing a dipyrrin moiety at the α-position of the confused pyrrole ring (1) was synthesized. PdII and BIII coordination at the peripheral prodigiosin-like moiety of 1 afforded the corresponding complexes 2 and 3. Reflux of 2 in triethylamine (TEA) converted the meso-phenyl into the PdII-coordinating phenoxy group to afford 4. Under the same reaction conditions, TEA was linked to the α-position of the dipyrrin unit in 3 as an N,N-diethylaminovinyl group to afford 5. Furthermore, peripheral coordination of BIII in 3 and 5 improved the planarity of the phlorin macrocycle and thus facilitated the coordination of AgIII at the inner cavity to afford 3-Ag and 5-Ag, respectively. These results provide an effective approach for developing unique porphyrinoids through peripheral coordination.
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U2 - 10.1002/anie.201913290
DO - 10.1002/anie.201913290
M3 - Article
C2 - 31709678
AN - SCOPUS:85076225433
SN - 1433-7851
VL - 59
SP - 1537
EP - 1541
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 4
ER -