Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors

Tze Gang Hsu; Ching Li Huang; Wen Ching Yin; Fong Yi Cao; Chia Wei Wang; Santosh K. Sahoo; Shao Ling Chang; Hsiao Chieh Chou; Yen-Ju Cheng

doi:10.1021/acs.orglett.1c00110

Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors

Tze Gang Hsu, Ching Li Huang, Wen Ching Yin, Fong Yi Cao, Chia Wei Wang, Santosh K. Sahoo, Shao Ling Chang, Hsiao Chieh Chou, Yen-Ju Cheng^*

^*Corresponding author for this work

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

4 Scopus citations

Abstract

We discovered a unique synthetic route to construct 2H-pyran-containing tetracyclic dithienocyclopentapyran (DTCP) and dibenzocyclopentapyran (DBCP) architectures. The synthesis involves an acid-induced dehydration cyclization followed by a [1,5] hydride-shift isomerization to form a cyclopentanone moiety which was converted to the pyran-embedded tetracyclic products by a CuI-catalyzed intramolecular C-O bond formation in good yield. DTCP was used as a building block to prepare an acceptor-donor-acceptor (A-D-A) type n-type material DTCP-BC leading to a solar cell efficiency of 9.32%.

Original language	English
Pages (from-to)	1692–1697
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.1c00110
State	Published - 5 Mar 2021

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Hsu, T. G., Huang, C. L., Yin, W. C., Cao, F. Y., Wang, C. W., Sahoo, S. K., Chang, S. L., Chou, H. C., & Cheng, Y.-J. (2021). Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors. Organic Letters, 23(5), 1692–1697. https://doi.org/10.1021/acs.orglett.1c00110

@article{658627a94c234881a548a9af9c15cbce,

title = "Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors",

abstract = "We discovered a unique synthetic route to construct 2H-pyran-containing tetracyclic dithienocyclopentapyran (DTCP) and dibenzocyclopentapyran (DBCP) architectures. The synthesis involves an acid-induced dehydration cyclization followed by a [1,5] hydride-shift isomerization to form a cyclopentanone moiety which was converted to the pyran-embedded tetracyclic products by a CuI-catalyzed intramolecular C-O bond formation in good yield. DTCP was used as a building block to prepare an acceptor-donor-acceptor (A-D-A) type n-type material DTCP-BC leading to a solar cell efficiency of 9.32%.",

author = "Hsu, {Tze Gang} and Huang, {Ching Li} and Yin, {Wen Ching} and Cao, {Fong Yi} and Wang, {Chia Wei} and Sahoo, {Santosh K.} and Chang, {Shao Ling} and Chou, {Hsiao Chieh} and Yen-Ju Cheng",

year = "2021",

month = mar,

day = "5",

doi = "10.1021/acs.orglett.1c00110",

language = "English",

volume = "23",

pages = "1692–1697",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

Hsu, TG, Huang, CL, Yin, WC, Cao, FY, Wang, CW, Sahoo, SK, Chang, SL, Chou, HC & Cheng, Y-J 2021, 'Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors', Organic Letters, vol. 23, no. 5, pp. 1692–1697. https://doi.org/10.1021/acs.orglett.1c00110

TY - JOUR

T1 - Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors

AU - Hsu, Tze Gang

AU - Huang, Ching Li

AU - Yin, Wen Ching

AU - Cao, Fong Yi

AU - Wang, Chia Wei

AU - Sahoo, Santosh K.

AU - Chang, Shao Ling

AU - Chou, Hsiao Chieh

AU - Cheng, Yen-Ju

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We discovered a unique synthetic route to construct 2H-pyran-containing tetracyclic dithienocyclopentapyran (DTCP) and dibenzocyclopentapyran (DBCP) architectures. The synthesis involves an acid-induced dehydration cyclization followed by a [1,5] hydride-shift isomerization to form a cyclopentanone moiety which was converted to the pyran-embedded tetracyclic products by a CuI-catalyzed intramolecular C-O bond formation in good yield. DTCP was used as a building block to prepare an acceptor-donor-acceptor (A-D-A) type n-type material DTCP-BC leading to a solar cell efficiency of 9.32%.

AB - We discovered a unique synthetic route to construct 2H-pyran-containing tetracyclic dithienocyclopentapyran (DTCP) and dibenzocyclopentapyran (DBCP) architectures. The synthesis involves an acid-induced dehydration cyclization followed by a [1,5] hydride-shift isomerization to form a cyclopentanone moiety which was converted to the pyran-embedded tetracyclic products by a CuI-catalyzed intramolecular C-O bond formation in good yield. DTCP was used as a building block to prepare an acceptor-donor-acceptor (A-D-A) type n-type material DTCP-BC leading to a solar cell efficiency of 9.32%.

UR - http://www.scopus.com/inward/record.url?scp=85101881909&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c00110

DO - 10.1021/acs.orglett.1c00110

M3 - Article

C2 - 33621105

AN - SCOPUS:85101881909

SN - 1523-7060

VL - 23

SP - 1692

EP - 1697

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors

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