Starphenes and Phenes: Structures and Properties
Abstract Acenes have been known for a long time but their larger congeners, starphenes and phenes, have only been recently accessible as processable and characterizable derivatives. In this personalized review, we delineate the synthetic approach developed by our group over the last four years. Nick...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag
2019-11-01
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| Series: | Organic Materials |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1700846 |
| _version_ | 1811289342766743552 |
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| author | Elias C. Rüdiger Matthias Müller Jan Freudenberg Uwe H. F. Bunz |
| author_facet | Elias C. Rüdiger Matthias Müller Jan Freudenberg Uwe H. F. Bunz |
| author_sort | Elias C. Rüdiger |
| collection | DOAJ |
| description | Abstract
Acenes have been known for a long time but their larger congeners, starphenes and phenes, have only been recently accessible as processable and characterizable derivatives. In this personalized review, we delineate the synthetic approach developed by our group over the last four years. Nickel-mediated Yamamoto coupling of ortho-dibromoacenes generates cyclotrimers. If performed in a shotgun approach, i.e. with substituted 2,3-dibromotetracene or -pentacene in the presence of ortho-dibromobenzene or ortho-dibromoveratrole, trimeric phenes and tetramers would result. Cyclotrimers formed by a pentacenylene and two phenylenes are formally dibenzo[a,c]hexacenes. A direct way to obtain these species is to employ Stille coupling of a dimethylstannafluorene with 2,3-dibromoacenes. If tetrabromoanthracenes or tetrabromopentacenes are fed into this process, tetrabenzopentacene and tetrabenzoheptacenes are easily accessible. Optical and quantum-chemical characterizations provide insight into the electronic situation and aromaticity of these species. |
| first_indexed | 2024-04-13T03:54:11Z |
| format | Article |
| id | doaj.art-7f0f9766835a4675b3510e698325ef40 |
| institution | Directory Open Access Journal |
| issn | 2625-1825 |
| language | English |
| last_indexed | 2024-04-13T03:54:11Z |
| publishDate | 2019-11-01 |
| publisher | Georg Thieme Verlag |
| record_format | Article |
| series | Organic Materials |
| spelling | doaj.art-7f0f9766835a4675b3510e698325ef402022-12-22T03:03:42ZengGeorg Thieme VerlagOrganic Materials2625-18252019-11-01010100101810.1055/s-0039-1700846Starphenes and Phenes: Structures and PropertiesElias C. Rüdiger0Matthias Müller1Jan Freudenberg2Uwe H. F. Bunz3Organisch-Chemisches Institut, Ruprecht-Karls-Universität HeidelbergOrganisch-Chemisches Institut, Ruprecht-Karls-Universität HeidelbergOrganisch-Chemisches Institut, Ruprecht-Karls-Universität HeidelbergOrganisch-Chemisches Institut, Ruprecht-Karls-Universität HeidelbergAbstract Acenes have been known for a long time but their larger congeners, starphenes and phenes, have only been recently accessible as processable and characterizable derivatives. In this personalized review, we delineate the synthetic approach developed by our group over the last four years. Nickel-mediated Yamamoto coupling of ortho-dibromoacenes generates cyclotrimers. If performed in a shotgun approach, i.e. with substituted 2,3-dibromotetracene or -pentacene in the presence of ortho-dibromobenzene or ortho-dibromoveratrole, trimeric phenes and tetramers would result. Cyclotrimers formed by a pentacenylene and two phenylenes are formally dibenzo[a,c]hexacenes. A direct way to obtain these species is to employ Stille coupling of a dimethylstannafluorene with 2,3-dibromoacenes. If tetrabromoanthracenes or tetrabromopentacenes are fed into this process, tetrabenzopentacene and tetrabenzoheptacenes are easily accessible. Optical and quantum-chemical characterizations provide insight into the electronic situation and aromaticity of these species.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1700846acenesphenesstarphenes |
| spellingShingle | Elias C. Rüdiger Matthias Müller Jan Freudenberg Uwe H. F. Bunz Starphenes and Phenes: Structures and Properties Organic Materials acenes phenes starphenes |
| title | Starphenes and Phenes: Structures and Properties |
| title_full | Starphenes and Phenes: Structures and Properties |
| title_fullStr | Starphenes and Phenes: Structures and Properties |
| title_full_unstemmed | Starphenes and Phenes: Structures and Properties |
| title_short | Starphenes and Phenes: Structures and Properties |
| title_sort | starphenes and phenes structures and properties |
| topic | acenes phenes starphenes |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1700846 |
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