N-Confused Hexapyrrolic Phlorinoid with NIR Absorption: Synthesis, Fusion, Oxidation, and Copper(II) Coordination

Yu Du; Bin Zhu; Qizhao Li; Glib Baryshnikov; Chuanwan Wei; Yingwu Lin; Guangxian Su; Chengjie Li; Hans Ågren; Yongshu Xie

doi:10.1021/acs.orglett.0c03710

N-Confused Hexapyrrolic Phlorinoid with NIR Absorption: Synthesis, Fusion, Oxidation, and Copper(II) Coordination

Yu Du
, Bin Zhu
, Qizhao Li^*
, Glib Baryshnikov
, Chuanwan Wei
, Yingwu Lin
, Guangxian Su
, Chengjie Li
, Hans Ågren
, Yongshu Xie^*

^*Corresponding author for this work

East China University of Science and Technology
KTH Royal Institute of Technology
University of South China
Hunan Normal University

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

An N-confused hexapyrrolic phlorinoid 1 and its isomer N-fused hexapyrrolic phlorinoid 2 were synthesized through [4 + 2] condensation. Both 1 and 2 can be readily transformed into N-confused hexapyrrolic phlorinone 3 under aerobic conditions. Coordination of 1 with Cu(acac)2 afforded two different mono-Cu(II) complexes 4 and 5 with CNNN and ONNN coordination environments, respectively. The NIR absorption bands can be effectively modulated up to 1265 nm through the oxidation, fusion, and metalation reactions.

Original language	English
Pages (from-to)	9648-9652
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.0c03710
State	Published - 18 Dec 2020
Externally published	Yes

Access to Document

10.1021/acs.orglett.0c03710

Cite this

@article{73558078cf744caab1c16c59255adb9e,

title = "N-Confused Hexapyrrolic Phlorinoid with NIR Absorption: Synthesis, Fusion, Oxidation, and Copper(II) Coordination",

abstract = "An N-confused hexapyrrolic phlorinoid 1 and its isomer N-fused hexapyrrolic phlorinoid 2 were synthesized through [4 + 2] condensation. Both 1 and 2 can be readily transformed into N-confused hexapyrrolic phlorinone 3 under aerobic conditions. Coordination of 1 with Cu(acac)2 afforded two different mono-Cu(II) complexes 4 and 5 with CNNN and ONNN coordination environments, respectively. The NIR absorption bands can be effectively modulated up to 1265 nm through the oxidation, fusion, and metalation reactions.",

author = "Yu Du and Bin Zhu and Qizhao Li and Glib Baryshnikov and Chuanwan Wei and Yingwu Lin and Guangxian Su and Chengjie Li and Hans {\AA}gren and Yongshu Xie",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = dec,

day = "18",

doi = "10.1021/acs.orglett.0c03710",

language = "英语",

volume = "22",

pages = "9648--9652",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - N-Confused Hexapyrrolic Phlorinoid with NIR Absorption

T2 - Synthesis, Fusion, Oxidation, and Copper(II) Coordination

AU - Du, Yu

AU - Zhu, Bin

AU - Li, Qizhao

AU - Baryshnikov, Glib

AU - Wei, Chuanwan

AU - Lin, Yingwu

AU - Su, Guangxian

AU - Li, Chengjie

AU - Ågren, Hans

AU - Xie, Yongshu

PY - 2020/12/18

Y1 - 2020/12/18

N2 - An N-confused hexapyrrolic phlorinoid 1 and its isomer N-fused hexapyrrolic phlorinoid 2 were synthesized through [4 + 2] condensation. Both 1 and 2 can be readily transformed into N-confused hexapyrrolic phlorinone 3 under aerobic conditions. Coordination of 1 with Cu(acac)2 afforded two different mono-Cu(II) complexes 4 and 5 with CNNN and ONNN coordination environments, respectively. The NIR absorption bands can be effectively modulated up to 1265 nm through the oxidation, fusion, and metalation reactions.

AB - An N-confused hexapyrrolic phlorinoid 1 and its isomer N-fused hexapyrrolic phlorinoid 2 were synthesized through [4 + 2] condensation. Both 1 and 2 can be readily transformed into N-confused hexapyrrolic phlorinone 3 under aerobic conditions. Coordination of 1 with Cu(acac)2 afforded two different mono-Cu(II) complexes 4 and 5 with CNNN and ONNN coordination environments, respectively. The NIR absorption bands can be effectively modulated up to 1265 nm through the oxidation, fusion, and metalation reactions.

UR - https://www.scopus.com/pages/publications/85097748542

U2 - 10.1021/acs.orglett.0c03710

DO - 10.1021/acs.orglett.0c03710

M3 - 文章

C2 - 33295779

AN - SCOPUS:85097748542

SN - 1523-7060

VL - 22

SP - 9648

EP - 9652

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

N-Confused Hexapyrrolic Phlorinoid with NIR Absorption: Synthesis, Fusion, Oxidation, and Copper(II) Coordination

Abstract

Access to Document

Other files and links

Fingerprint

Cite this