Fluorenyl Based Macrocyclic Polyradicaloids
Synthesis of stable open-shell polyradicaloids including control of intramolecular spin–spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In...
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| Published in | Journal of the American Chemical Society Vol. 139; no. 37; pp. 13173 - 13183 |
|---|---|
| Main Authors | , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
20.09.2017
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | Synthesis of stable open-shell polyradicaloids including control of intramolecular spin–spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In one series (FR-MCn, n = 4–6), the fluorenyl radicals are directly linked at 3,6-positions; whereas in the other series (MC-FnAn, n = 3–5), an additional ethynylene moiety is inserted between the neighboring fluorenyl units. To access stable macrocyclic polyradicaloids, three synthetic methods were developed. All of these stable macrocycles can be purified by normal silica gel column chromatography under ambient conditions. In all cases, moderate polyradical characters were calculated by restricted active space spin-flip method due to the moderate intramolecular antiferromagnetic spin–spin interactions. The excitation energies from the low-spin ground state to the lowest high-spin excited state were evaluated by superconducting quantum interference device measurements. Their physical properties were also compared with the respective linear fluorenyl radical oligomers (FR-n, n = 3–6). It is found that the geometry, i.e., the distortional angle and spacer (w or w/o ethynylene) between the neighboring fluorenyl units, has significant effect on their polyradical character, excitation energy, one-photon absorption, two-photon absorption and electrochemical properties. In addition, the macrocyclic tetramers FR-MC4 and MC-F4A4 showed global antiaromatic character due to cyclic π-conjugation with 36 and 44 π-electrons, respectively. |
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| AbstractList | Synthesis of stable open-shell polyradicaloids including control of intramolecular spin-spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In one series (FR-MCn, n = 4-6), the fluorenyl radicals are directly linked at 3,6-positions; whereas in the other series (MC-FnAn, n = 3-5), an additional ethynylene moiety is inserted between the neighboring fluorenyl units. To access stable macrocyclic polyradicaloids, three synthetic methods were developed. All of these stable macrocycles can be purified by normal silica gel column chromatography under ambient conditions. In all cases, moderate polyradical characters were calculated by restricted active space spin-flip method due to the moderate intramolecular antiferromagnetic spin-spin interactions. The excitation energies from the low-spin ground state to the lowest high-spin excited state were evaluated by superconducting quantum interference device measurements. Their physical properties were also compared with the respective linear fluorenyl radical oligomers (FR-n, n = 3-6). It is found that the geometry, i.e., the distortional angle and spacer (w or w/o ethynylene) between the neighboring fluorenyl units, has significant effect on their polyradical character, excitation energy, one-photon absorption, two-photon absorption and electrochemical properties. In addition, the macrocyclic tetramers FR-MC4 and MC-F4A4 showed global antiaromatic character due to cyclic π-conjugation with 36 and 44 π-electrons, respectively. Synthesis of stable open-shell polyradicaloids including control of intramolecular spin-spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In one series (FR-MCn, n = 4-6), the fluorenyl radicals are directly linked at 3,6-positions; whereas in the other series (MC-FnAn, n = 3-5), an additional ethynylene moiety is inserted between the neighboring fluorenyl units. To access stable macrocyclic polyradicaloids, three synthetic methods were developed. All of these stable macrocycles can be purified by normal silica gel column chromatography under ambient conditions. In all cases, moderate polyradical characters were calculated by restricted active space spin-flip method due to the moderate intramolecular antiferromagnetic spin-spin interactions. The excitation energies from the low-spin ground state to the lowest high-spin excited state were evaluated by superconducting quantum interference device measurements. Their physical properties were also compared with the respective linear fluorenyl radical oligomers (FR-n, n = 3-6). It is found that the geometry, i.e., the distortional angle and spacer (w or w/o ethynylene) between the neighboring fluorenyl units, has significant effect on their polyradical character, excitation energy, one-photon absorption, two-photon absorption and electrochemical properties. In addition, the macrocyclic tetramers FR-MC4 and MC-F4A4 showed global antiaromatic character due to cyclic pi-conjugation with 36 and 44 pi-electrons, respectively. Synthesis of stable open-shell polyradicaloids including control of intramolecular spin-spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In one series (FR-MCn, n = 4-6), the fluorenyl radicals are directly linked at 3,6-positions; whereas in the other series (MC-FnAn, n = 3-5), an additional ethynylene moiety is inserted between the neighboring fluorenyl units. To access stable macrocyclic polyradicaloids, three synthetic methods were developed. All of these stable macrocycles can be purified by normal silica gel column chromatography under ambient conditions. In all cases, moderate polyradical characters were calculated by restricted active space spin-flip method due to the moderate intramolecular antiferromagnetic spin-spin interactions. The excitation energies from the low-spin ground state to the lowest high-spin excited state were evaluated by superconducting quantum interference device measurements. Their physical properties were also compared with the respective linear fluorenyl radical oligomers (FR-n, n = 3-6). It is found that the geometry, i.e., the distortional angle and spacer (w or w/o ethynylene) between the neighboring fluorenyl units, has significant effect on their polyradical character, excitation energy, one-photon absorption, two-photon absorption and electrochemical properties. In addition, the macrocyclic tetramers FR-MC4 and MC-F4A4 showed global antiaromatic character due to cyclic π-conjugation with 36 and 44 π-electrons, respectively.Synthesis of stable open-shell polyradicaloids including control of intramolecular spin-spin interactions is a challenging topic in organic chemistry and materials science. Herein, we report the synthesis and physical characterization of two series of fluorenyl based macrocyclic polyradicaloids. In one series (FR-MCn, n = 4-6), the fluorenyl radicals are directly linked at 3,6-positions; whereas in the other series (MC-FnAn, n = 3-5), an additional ethynylene moiety is inserted between the neighboring fluorenyl units. To access stable macrocyclic polyradicaloids, three synthetic methods were developed. All of these stable macrocycles can be purified by normal silica gel column chromatography under ambient conditions. In all cases, moderate polyradical characters were calculated by restricted active space spin-flip method due to the moderate intramolecular antiferromagnetic spin-spin interactions. The excitation energies from the low-spin ground state to the lowest high-spin excited state were evaluated by superconducting quantum interference device measurements. Their physical properties were also compared with the respective linear fluorenyl radical oligomers (FR-n, n = 3-6). It is found that the geometry, i.e., the distortional angle and spacer (w or w/o ethynylene) between the neighboring fluorenyl units, has significant effect on their polyradical character, excitation energy, one-photon absorption, two-photon absorption and electrochemical properties. In addition, the macrocyclic tetramers FR-MC4 and MC-F4A4 showed global antiaromatic character due to cyclic π-conjugation with 36 and 44 π-electrons, respectively. |
| Author | Osuka, Atsuhiro Sandoval-Salinas, María Eugenia Ding, Jun Wu, Jishan Lu, Xuefeng Phan, Hoa Tanaka, Takayuki Gopalakrishna, Tullimilli Y Lee, Sangsu Herng, Tun Seng Hong, Yongseok Kim, Dongho Zeng, Wangdong Casanova, David |
| AuthorAffiliation | Department of Chemistry Kyoto University Kimika Fakultatea, Euskal Herriko Unibertsitatea & Donostia International Physics Center Department of Materials Science & Engineering IKERBASQUE - Basque Foundation for Science Departament de Ciència de Materials i Química Física, Institut de Química Teòrica i Computacional (IQTCUB) Yonsei University Universitat de Barcelona Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry Department of Chemistry, Graduate School of Science |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Kyoto University – name: Universitat de Barcelona – name: IKERBASQUE - Basque Foundation for Science – name: Kimika Fakultatea, Euskal Herriko Unibertsitatea & Donostia International Physics Center – name: Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry – name: Department of Materials Science & Engineering – name: Departament de Ciència de Materials i Química Física, Institut de Química Teòrica i Computacional (IQTCUB) – name: Department of Chemistry, Graduate School of Science – name: Yonsei University |
| Author_xml | – sequence: 1 givenname: Xuefeng surname: Lu fullname: Lu, Xuefeng organization: Department of Chemistry – sequence: 2 givenname: Sangsu surname: Lee fullname: Lee, Sangsu organization: Yonsei University – sequence: 3 givenname: Yongseok surname: Hong fullname: Hong, Yongseok organization: Yonsei University – sequence: 4 givenname: Hoa surname: Phan fullname: Phan, Hoa organization: Department of Chemistry – sequence: 5 givenname: Tullimilli Y surname: Gopalakrishna fullname: Gopalakrishna, Tullimilli Y organization: Department of Chemistry – sequence: 6 givenname: Tun Seng surname: Herng fullname: Herng, Tun Seng organization: Department of Materials Science & Engineering – sequence: 7 givenname: Takayuki surname: Tanaka fullname: Tanaka, Takayuki organization: Kyoto University – sequence: 8 givenname: María Eugenia surname: Sandoval-Salinas fullname: Sandoval-Salinas, María Eugenia organization: Kimika Fakultatea, Euskal Herriko Unibertsitatea & Donostia International Physics Center – sequence: 9 givenname: Wangdong surname: Zeng fullname: Zeng, Wangdong organization: Department of Chemistry – sequence: 10 givenname: Jun surname: Ding fullname: Ding, Jun organization: Department of Materials Science & Engineering – sequence: 11 givenname: David surname: Casanova fullname: Casanova, David organization: IKERBASQUE - Basque Foundation for Science – sequence: 12 givenname: Atsuhiro orcidid: 0000-0001-8697-8488 surname: Osuka fullname: Osuka, Atsuhiro organization: Kyoto University – sequence: 13 givenname: Dongho orcidid: 0000-0001-8668-2644 surname: Kim fullname: Kim, Dongho email: dongho@yonsei.ac.kr organization: Yonsei University – sequence: 14 givenname: Jishan orcidid: 0000-0002-8231-0437 surname: Wu fullname: Wu, Jishan email: chmwuj@nus.edu.sg organization: Department of Chemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28840723$$D View this record in MEDLINE/PubMed |
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| Keywords | QUINOIDAL OLIGOTHIOPHENES POLYCYCLIC AROMATIC-HYDROCARBON GROUND-STATE BIRADICALOID CHARACTER 2ND HYPERPOLARIZABILITIES OPEN-SHELL CLOSED-SHELL CHAIN-LENGTH EXTENDED P-QUINODIMETHANES DIRADICAL CHARACTER |
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| Snippet | Synthesis of stable open-shell polyradicaloids including control of intramolecular spin–spin interactions is a challenging topic in organic chemistry and... Synthesis of stable open-shell polyradicaloids including control of intramolecular spin-spin interactions is a challenging topic in organic chemistry and... |
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| Title | Fluorenyl Based Macrocyclic Polyradicaloids |
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