Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity

Yue Xu; Bin Zhu; Lingfang Zhang; Glib Baryshnikov; Feng Sha; Emiko Nishimoto; Hideaki Takano; Chengjie Li; Xinyan Wu; Hans Ågren; Hiroshi Shinokubo; Yongshu Xie; Qizhao Li

doi:10.1021/acs.orglett.3c04323

Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity

Yue Xu
, Bin Zhu
, Lingfang Zhang
, Glib Baryshnikov
, Feng Sha
, Emiko Nishimoto
, Hideaki Takano
, Chengjie Li
, Xinyan Wu
, Hans Ågren
, Hiroshi Shinokubo
, Yongshu Xie^*
, Qizhao Li^*

^*Corresponding author for this work

East China University of Science and Technology
Linköping University
Nagoya University
Uppsala University

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

7 Scopus citations

Abstract

Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the α-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl₂ in tetrahydrofuran/H₂O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.

Original language	English
Pages (from-to)	571-576
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.3c04323
State	Published - 19 Jan 2024
Externally published	Yes

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10.1021/acs.orglett.3c04323

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title = "Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity",

abstract = "Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the α-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl2 in tetrahydrofuran/H2O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.",

author = "Yue Xu and Bin Zhu and Lingfang Zhang and Glib Baryshnikov and Feng Sha and Emiko Nishimoto and Hideaki Takano and Chengjie Li and Xinyan Wu and Hans {\AA}gren and Hiroshi Shinokubo and Yongshu Xie and Qizhao Li",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = jan,

day = "19",

doi = "10.1021/acs.orglett.3c04323",

language = "英语",

volume = "26",

pages = "571--576",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "2",

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TY - JOUR

T1 - Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity

AU - Xu, Yue

AU - Zhu, Bin

AU - Zhang, Lingfang

AU - Baryshnikov, Glib

AU - Sha, Feng

AU - Nishimoto, Emiko

AU - Takano, Hideaki

AU - Li, Chengjie

AU - Wu, Xinyan

AU - Ågren, Hans

AU - Shinokubo, Hiroshi

AU - Xie, Yongshu

AU - Li, Qizhao

PY - 2024/1/19

Y1 - 2024/1/19

N2 - Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the α-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl2 in tetrahydrofuran/H2O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.

AB - Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the α-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl2 in tetrahydrofuran/H2O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.

UR - https://www.scopus.com/pages/publications/85182578129

U2 - 10.1021/acs.orglett.3c04323

DO - 10.1021/acs.orglett.3c04323

M3 - 文章

C2 - 38190656

AN - SCOPUS:85182578129

SN - 1523-7060

VL - 26

SP - 571

EP - 576

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity

Abstract

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