A Rational Approach to Tetra‐Functional Photo‐Switches
Abstract α,ω‐Bis(1,8‐dichloroanthracen‐10‐yl)alkanes with (CH2)n‐linker units (n=1–4) were synthesized starting from 1,8‐dichloroanthracen‐10(9H)‐one. This was transformed into anthracenes with allyl, bromomethyl and propargyl substituents in position 10; these were converted in various C−C‐bond for...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2019-03-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.201900029 |
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| author | Dr. Philipp Niermeier Dr. Jan‐Hendrik Lamm Dr. Andreas Mix Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel |
| author_facet | Dr. Philipp Niermeier Dr. Jan‐Hendrik Lamm Dr. Andreas Mix Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel |
| author_sort | Dr. Philipp Niermeier |
| collection | DOAJ |
| description | Abstract α,ω‐Bis(1,8‐dichloroanthracen‐10‐yl)alkanes with (CH2)n‐linker units (n=1–4) were synthesized starting from 1,8‐dichloroanthracen‐10(9H)‐one. This was transformed into anthracenes with allyl, bromomethyl and propargyl substituents in position 10; these were converted in various C−C‐bond formation reactions (plus hydrogenation), leading to two anthracene units flexibly linked by α,ω‐alkandiyl groups. 1,2‐Ethandiyl‐ and 1,3‐propandiyl‐linked derivatives were functionalized with ethynyl groups in positions 1, 8, 1’ and 8’, and these terminally functionalized by Me3Sn groups using Me2NSnMe3. All linked bisanthracenes were subjected to UV light induced cyclomerization and a series of 9,10 : 9’,10’‐photo‐cyclomers were obtained. Their thermal cycloreversion and (repeated) switchability was demonstrated. 1,3‐Bis{1,8‐bis[(trimethylstannyl)ethynyl]anthracen‐10‐yl}propane served as model compound for photo‐switchable acceptor molecules and its open and closed forms were characterized by NMR and DOSY experiments. |
| first_indexed | 2024-03-12T21:33:46Z |
| format | Article |
| id | doaj.art-a5b1d03ebfda456ab40feb60480566b9 |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-03-12T21:33:46Z |
| publishDate | 2019-03-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-a5b1d03ebfda456ab40feb60480566b92023-07-27T14:18:46ZengWiley-VCHChemistryOpen2191-13632019-03-018330431510.1002/open.201900029A Rational Approach to Tetra‐Functional Photo‐SwitchesDr. Philipp Niermeier0Dr. Jan‐Hendrik Lamm1Dr. Andreas Mix2Beate Neumann3Dr. Hans‐Georg Stammler4Prof. Dr. Norbert W. Mitzel5Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyUniversität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyUniversität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyUniversität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyUniversität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyUniversität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld GermanyAbstract α,ω‐Bis(1,8‐dichloroanthracen‐10‐yl)alkanes with (CH2)n‐linker units (n=1–4) were synthesized starting from 1,8‐dichloroanthracen‐10(9H)‐one. This was transformed into anthracenes with allyl, bromomethyl and propargyl substituents in position 10; these were converted in various C−C‐bond formation reactions (plus hydrogenation), leading to two anthracene units flexibly linked by α,ω‐alkandiyl groups. 1,2‐Ethandiyl‐ and 1,3‐propandiyl‐linked derivatives were functionalized with ethynyl groups in positions 1, 8, 1’ and 8’, and these terminally functionalized by Me3Sn groups using Me2NSnMe3. All linked bisanthracenes were subjected to UV light induced cyclomerization and a series of 9,10 : 9’,10’‐photo‐cyclomers were obtained. Their thermal cycloreversion and (repeated) switchability was demonstrated. 1,3‐Bis{1,8‐bis[(trimethylstannyl)ethynyl]anthracen‐10‐yl}propane served as model compound for photo‐switchable acceptor molecules and its open and closed forms were characterized by NMR and DOSY experiments.https://doi.org/10.1002/open.201900029AnthracenesC−C-Bond FormationPhotocyclomerizationCycloreversionPhoto-switches |
| spellingShingle | Dr. Philipp Niermeier Dr. Jan‐Hendrik Lamm Dr. Andreas Mix Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel A Rational Approach to Tetra‐Functional Photo‐Switches ChemistryOpen Anthracenes C−C-Bond Formation Photocyclomerization Cycloreversion Photo-switches |
| title | A Rational Approach to Tetra‐Functional Photo‐Switches |
| title_full | A Rational Approach to Tetra‐Functional Photo‐Switches |
| title_fullStr | A Rational Approach to Tetra‐Functional Photo‐Switches |
| title_full_unstemmed | A Rational Approach to Tetra‐Functional Photo‐Switches |
| title_short | A Rational Approach to Tetra‐Functional Photo‐Switches |
| title_sort | rational approach to tetra functional photo switches |
| topic | Anthracenes C−C-Bond Formation Photocyclomerization Cycloreversion Photo-switches |
| url | https://doi.org/10.1002/open.201900029 |
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