Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review
Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Poly...
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| Published in | RSC advances Vol. 11; no. 51; pp. 32158 - 3222 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
29.09.2021
The Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C-C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf)
2
/AlCl
3
, FeCl
3
, MoCl
5
, PIFA/BF
3
-Et
2
O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein.
Nanographenes have been attracting increasing attention owing to their widespread applications in organic electronics. Polycyclic aromatic hydrocarbons are popular research subjects due to their high stability, planar structure and optical spectra. |
|---|---|
| AbstractList | Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C–C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf)₂/AlCl₃, FeCl₃, MoCl₅, PIFA/BF₃–Et₂O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C–C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf) 2 /AlCl 3 , FeCl 3 , MoCl 5 , PIFA/BF 3 –Et 2 O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. Nanographenes have been attracting increasing attention owing to their widespread applications in organic electronics. Polycyclic aromatic hydrocarbons are popular research subjects due to their high stability, planar structure and optical spectra. Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C-C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf)2/AlCl3, FeCl3, MoCl5, PIFA/BF3-Et2O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein.Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C-C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf)2/AlCl3, FeCl3, MoCl5, PIFA/BF3-Et2O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C–C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf) 2 /AlCl 3 , FeCl 3 , MoCl 5 , PIFA/BF 3 –Et 2 O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C–C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf)2/AlCl3, FeCl3, MoCl5, PIFA/BF3–Et2O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic electronics. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. Polycyclic aromatic hydrocarbons (PAHs) are popular research subjects due to their high stability, rigid planar structure, and characteristic optical spectra. The recent discovery of graphene, which can be regarded as giant PAH, has further stimulated research interest in this area. Chemists working with nanographene and heterocyclic analogs thereof have chosen it as their preferred tool for the assembly of large and complex architectures. The Scholl reaction has maintained significant relevance in contemporary organic synthesis with many advances in recent years and now ranks among the most useful C-C bond-forming processes for the generation of the π-conjugated frameworks of nanographene or their heterocyclic analogs. A broad range of oxidants and Lewis acids have found use in Scholl-type processes, including Cu(OTf) /AlCl , FeCl , MoCl , PIFA/BF -Et O, and DDQ, in combination with Brønsted or Lewis acids, and the surface-mediated reaction has found especially wide applications in PAH synthesis. Undoubtedly, the utility of the Scholl reaction is supreme in the construction of nanographene and their heterocyclic analogues. The detailed analysis of the progress achieved in this field reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface-assisted cyclodehydrogenation and developing new reagents. In this review, we highlight and discuss the recent modifications in the Scholl reaction for nanographene synthesis using numerous oxidant systems. In addition, the merits or demerits of each oxidative reagent is described herein. |
| Author | Naeem, Nafeesa Sadiq, Amina Mughal, Ehsan Ullah Ahmed, Saleh A Moussa, Ziad Alsantali, Reem I Al-Rooqi, Munirah M Jassas, Rabab S |
| AuthorAffiliation | Department of Pharmaceutical Chemistry United Arab Emirates University Assiut University Jamoum University College College of Science Faculty of Science College of Pharmacy Govt. College Women University Department of Chemistry University of Gujrat Faculty of Applied Science Chemistry Department Umm Al-Qura University Taif University Research Laboratories Unit |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Faculty of Applied Science – name: Research Laboratories Unit – name: Assiut University – name: Umm Al-Qura University – name: College of Pharmacy – name: United Arab Emirates University – name: Faculty of Science – name: Taif University – name: Govt. College Women University – name: Department of Pharmaceutical Chemistry – name: Chemistry Department – name: Jamoum University College – name: College of Science – name: University of Gujrat |
| Author_xml | – sequence: 1 givenname: Rabab S surname: Jassas fullname: Jassas, Rabab S – sequence: 2 givenname: Ehsan Ullah surname: Mughal fullname: Mughal, Ehsan Ullah – sequence: 3 givenname: Amina surname: Sadiq fullname: Sadiq, Amina – sequence: 4 givenname: Reem I surname: Alsantali fullname: Alsantali, Reem I – sequence: 5 givenname: Munirah M surname: Al-Rooqi fullname: Al-Rooqi, Munirah M – sequence: 6 givenname: Nafeesa surname: Naeem fullname: Naeem, Nafeesa – sequence: 7 givenname: Ziad surname: Moussa fullname: Moussa, Ziad – sequence: 8 givenname: Saleh A surname: Ahmed fullname: Ahmed, Saleh A |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35495486$$D View this record in MEDLINE/PubMed |
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| Notes | Saleh A. Ahmed was born in Assiut, Egypt in 1968 where is undertook undergraduate and postgraduate studies. He received his Bachelor and MSc from Assiut University, Egypt and PhD in photochemistry (photochromism) under the supervision of Prof. Heinz Dürr in Saarland University, Saarbrücken, Germany. He worked as postdoctoral fellow, senior researcher and visiting professor in France (CNRS fellow), Japan (JSPS fellow), Germany (AvH, DFG and DAAD fellows), Italy (TEMPUS fellow) and USA (Arab fund fellow). His current research interests include synthesis and photophysical properties of novel organic compounds, electronic devices and solar energy conversion, fluorophores with unique applications. Ehsan Ullah Mughal was born in Wazirabad, Pakistan, in 1978 and obtained his Master's degree from Quaid-e-Azam University, Islamabad, Pakistan, in organic chemistry. He obtained his PhD in 2013 from Bielefeld University, Germany, under the supervision of Prof. Dr Dietmar Kuck. For postdoctoral studies, he joined the group of Prof. Dr Xinliang Feng, Max Planck Institute for Polymer Research, Mainz, Germany. In 2015, he started his independent research group at the Department of Chemistry, University of Gujrat, Gujrat, Pakistan. His current research interests focus on the design and synthesis of bioactive heterocycles, synthetic flavonoids, transition metals-based terpyridine complexes, and their fabrication in DSSCs and organic functional materials for applications in organic electronics. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 ObjectType-Review-3 |
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| Snippet | Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting increasing attention owing to their widespread applications in organic... |
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| SubjectTerms | Aluminum chloride Analogs Chemical synthesis Chemistry Chemists Covalent bonds electronics Ferric chloride Graphene heterocyclic compounds Organic chemistry oxidants Oxidizing agents Planar structures Polycyclic aromatic hydrocarbons Reagents systematic review |
| Title | Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review |
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