Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties
Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Wang, Yang [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2023 |
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| Anmerkung: |
© Science China Press 2023 |
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| Übergeordnetes Werk: |
Enthalten in: Science in China - Asheville, NC : Science in China Press, 1995, 66(2023), 5 vom: 10. Apr., Seite 1450-1456 |
|---|---|
| Übergeordnetes Werk: |
volume:66 ; year:2023 ; number:5 ; day:10 ; month:04 ; pages:1450-1456 |
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| DOI / URN: |
10.1007/s11426-022-1503-1 |
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| 520 | |a Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. | ||
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| 700 | 1 | |a Li, Yang |4 aut | |
| 700 | 1 | |a Qie, Fengxiang |4 aut | |
| 700 | 1 | |a Shi, Chunfeng |4 aut | |
| 700 | 1 | |a Zhang, Lei |4 aut | |
| 700 | 1 | |a Zhen, Yonggang |4 aut | |
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10.1007/s11426-022-1503-1 doi (DE-627)SPR052483460 (SPR)s11426-022-1503-1-e DE-627 ger DE-627 rakwb eng Wang, Yang verfasserin aut Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Science China Press 2023 Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. Hu, Yang aut Guo, Junfeng aut Wang, Zongrui aut Li, Yang aut Qie, Fengxiang aut Shi, Chunfeng aut Zhang, Lei aut Zhen, Yonggang aut Enthalten in Science in China Asheville, NC : Science in China Press, 1995 66(2023), 5 vom: 10. Apr., Seite 1450-1456 (DE-627)327310405 (DE-600)2043454-6 1862-2771 nnns volume:66 year:2023 number:5 day:10 month:04 pages:1450-1456 https://dx.doi.org/10.1007/s11426-022-1503-1 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_152 GBV_ILN_161 GBV_ILN_171 GBV_ILN_187 GBV_ILN_224 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 AR 66 2023 5 10 04 1450-1456 |
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10.1007/s11426-022-1503-1 doi (DE-627)SPR052483460 (SPR)s11426-022-1503-1-e DE-627 ger DE-627 rakwb eng Wang, Yang verfasserin aut Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Science China Press 2023 Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. Hu, Yang aut Guo, Junfeng aut Wang, Zongrui aut Li, Yang aut Qie, Fengxiang aut Shi, Chunfeng aut Zhang, Lei aut Zhen, Yonggang aut Enthalten in Science in China Asheville, NC : Science in China Press, 1995 66(2023), 5 vom: 10. Apr., Seite 1450-1456 (DE-627)327310405 (DE-600)2043454-6 1862-2771 nnns volume:66 year:2023 number:5 day:10 month:04 pages:1450-1456 https://dx.doi.org/10.1007/s11426-022-1503-1 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_152 GBV_ILN_161 GBV_ILN_171 GBV_ILN_187 GBV_ILN_224 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 AR 66 2023 5 10 04 1450-1456 |
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10.1007/s11426-022-1503-1 doi (DE-627)SPR052483460 (SPR)s11426-022-1503-1-e DE-627 ger DE-627 rakwb eng Wang, Yang verfasserin aut Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Science China Press 2023 Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. Hu, Yang aut Guo, Junfeng aut Wang, Zongrui aut Li, Yang aut Qie, Fengxiang aut Shi, Chunfeng aut Zhang, Lei aut Zhen, Yonggang aut Enthalten in Science in China Asheville, NC : Science in China Press, 1995 66(2023), 5 vom: 10. Apr., Seite 1450-1456 (DE-627)327310405 (DE-600)2043454-6 1862-2771 nnns volume:66 year:2023 number:5 day:10 month:04 pages:1450-1456 https://dx.doi.org/10.1007/s11426-022-1503-1 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_152 GBV_ILN_161 GBV_ILN_171 GBV_ILN_187 GBV_ILN_224 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 AR 66 2023 5 10 04 1450-1456 |
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10.1007/s11426-022-1503-1 doi (DE-627)SPR052483460 (SPR)s11426-022-1503-1-e DE-627 ger DE-627 rakwb eng Wang, Yang verfasserin aut Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Science China Press 2023 Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. Hu, Yang aut Guo, Junfeng aut Wang, Zongrui aut Li, Yang aut Qie, Fengxiang aut Shi, Chunfeng aut Zhang, Lei aut Zhen, Yonggang aut Enthalten in Science in China Asheville, NC : Science in China Press, 1995 66(2023), 5 vom: 10. Apr., Seite 1450-1456 (DE-627)327310405 (DE-600)2043454-6 1862-2771 nnns volume:66 year:2023 number:5 day:10 month:04 pages:1450-1456 https://dx.doi.org/10.1007/s11426-022-1503-1 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_152 GBV_ILN_161 GBV_ILN_171 GBV_ILN_187 GBV_ILN_224 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 AR 66 2023 5 10 04 1450-1456 |
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10.1007/s11426-022-1503-1 doi (DE-627)SPR052483460 (SPR)s11426-022-1503-1-e DE-627 ger DE-627 rakwb eng Wang, Yang verfasserin aut Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Science China Press 2023 Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. Hu, Yang aut Guo, Junfeng aut Wang, Zongrui aut Li, Yang aut Qie, Fengxiang aut Shi, Chunfeng aut Zhang, Lei aut Zhen, Yonggang aut Enthalten in Science in China Asheville, NC : Science in China Press, 1995 66(2023), 5 vom: 10. Apr., Seite 1450-1456 (DE-627)327310405 (DE-600)2043454-6 1862-2771 nnns volume:66 year:2023 number:5 day:10 month:04 pages:1450-1456 https://dx.doi.org/10.1007/s11426-022-1503-1 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_152 GBV_ILN_161 GBV_ILN_171 GBV_ILN_187 GBV_ILN_224 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 AR 66 2023 5 10 04 1450-1456 |
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copper-promoted domino cyanation/ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties |
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Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties |
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Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. © Science China Press 2023 |
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Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. © Science China Press 2023 |
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Abstract Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors. However, scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension, although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene. Herein, for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides (ANIs) with varied optoelectronic properties. Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs. The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the five-membered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects. By altering the functional units, the optical and electrical characteristics have been tailored rationally; thus p, n or ambipolar semiconducting properties can be achieved for the ANI derivatives. This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension, which is promising for applications in organic electronics. © Science China Press 2023 |
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