The Precise Synthesis of Phenylene-Extended Cyclic Hexa-peri-hexabenzocoronenes from Polyarylated [n]Cycloparaphenylenes by the Scholl Reaction
The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is de...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 35; pp. 10341 - 10346 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
24.08.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain‐induced side reactions during the oxidative cyclodehydrogenation and cyclic para‐hexa‐peri‐hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted.
All that it′s cutout to be: Polyarylated [n]cycloparaphenylenes are intermediates on the way to ultra‐short carbon nanotubes (CNT). Different polyarylated [n]CPPs can be prepared and their oxidative cyclodehydrogenation leads to CPPs that are cutouts from CNTs. |
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| AbstractList | The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom-up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain-induced side reactions during the oxidative cyclodehydrogenation and cyclic para-hexa-peri-hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted. The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain‐induced side reactions during the oxidative cyclodehydrogenation and cyclic para ‐hexa‐ peri ‐hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted. The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom-up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain-induced side reactions during the oxidative cyclodehydrogenation and cyclic para-hexa-peri-hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted. All that it's cutout to be: Polyarylated [n]cycloparaphenylenes are intermediates on the way to ultra-short carbon nanotubes (CNT). Different polyarylated [n]CPPs can be prepared and their oxidative cyclodehydrogenation leads to CPPs that are cutouts from CNTs. The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain‐induced side reactions during the oxidative cyclodehydrogenation and cyclic para‐hexa‐peri‐hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted. All that it′s cutout to be: Polyarylated [n]cycloparaphenylenes are intermediates on the way to ultra‐short carbon nanotubes (CNT). Different polyarylated [n]CPPs can be prepared and their oxidative cyclodehydrogenation leads to CPPs that are cutouts from CNTs. |
| Author | Wagner, Manfred Räder, Hans-Joachim Müllen, Klaus Golling, Florian E. Quernheim, Martin Zhang, Wen Nishiuchi, Tomohiko |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26110414$$D View this record in MEDLINE/PubMed |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | ELECTRONIC-PROPERTIES GRAPHENE NANORIBBONS CRYSTAL-STRUCTURE Scholl reaction polycyclic aromatic hydrocarbons WALLED CARBON NANOTUBES cycloparaphenylene carbon nanotubes FLUORESCENCE macrocycles CYCLOPARAPHENYLENES SELECTIVE SYNTHESIS EFFICIENT HYDROCARBON BOTTOM-UP SYNTHESIS |
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| Notes | DFG - No. MU 334/36-1 EU - No. FP 7 256617 MOLESOL This work was supported by the EU FP 7 256617 MOLESOL and the DFG project MU 334/36-1. F.E.G. thanks the Graduate School MAINZ for a scholarship. istex:D7A1618308FB1B19721A5174F314501FB31A1076 ArticleID:ANIE201500392 ark:/67375/WNG-V2JHLNHT-T Graduate School MAINZ This work was supported by the EU FP 7 256617 MOLESOL and the DFG project MU 334/36‐1. F.E.G. thanks the Graduate School MAINZ for a scholarship. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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(000360216800053.50) 2009; 121 Omachi, H (WOS:000321042600008) 2013; 5 Iyer, V. S. (000360216800053.20) 1998; 110 Schwab, MG (WOS:000310720900005) 2012; 134 Hitosugi, S (WOS:000306942600030) 2012; 134 FRIEDERICH, R (WOS:A1993LP07400031) 1993; 126 Golling, FE (WOS:000330558400008) 2014; 53 Jones, DJ (WOS:000306573800007) 2012; 48 Yamago, S (WOS:000274424000016) 2010; 49 Konishi, A (WOS:000314492500045) 2013; 135 Adamska, L (WOS:000345723800081) 2014; 14 Wasserfallen, D (WOS:000234941100060) 2006; 128 Konishi, A (WOS:000321173500007) 2013; 42 Yagi, A (WOS:000301161500031) 2012; 134 Hitosugi, S (WOS:000296787300005) 2011; 2 Sanchez-Valencia, JR (WOS:000339908000031) 2014; 512 Yamago, S. 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(000360216800053.5) 2011; 123 Evans, PJ (WOS:000334919700010) 2014; 6 Golling, F. E. (000360216800053.13) 2014; 126 Jasti, R (WOS:000263320900008) 2008; 130 Kammermeier, S (WOS:A1996VZ59200024) 1996; 35 Nishiuchi, T (WOS:000312552300005) 2012; 18 Draper, SM (WOS:000174844700003) 2002; 124 |
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| Snippet | The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of... The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom-up synthesis of... |
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| SubjectTerms | Benzene Carbon nanotubes Chemistry Chemistry, Multidisciplinary cycloparaphenylene macrocycles Nanotechnology Nanotubes Physical Sciences polycyclic aromatic hydrocarbons Scholl reaction Science & Technology Synthesis Trimers |
| Title | The Precise Synthesis of Phenylene-Extended Cyclic Hexa-peri-hexabenzocoronenes from Polyarylated [n]Cycloparaphenylenes by the Scholl Reaction |
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