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Stable 2D anti-ferromagnetically coupled fluorenyl radical dendrons
Wang, Jian,Kim, Gakhyun,Sandoval-Salinas, Marí,a Eugenia,Phan, Hoa,Gopalakrishna, Tullimilli Y.,Lu, Xuefeng,Casanova, David,Kim, Dongho,Wu, Jishan Royal Society of Chemistry 2018 Chemical Science Vol.9 No.13
<▼1><P>The first class of stable two-dimensional anti-ferromagnetically coupled dendritic polyradicaloids was synthesized, which show polyradical character and unique properties.</P></▼1><▼2><P>We report the first class of stable, two-dimensional (2D) anti-ferromagnetically coupled dendritic polyradicaloids. A kinetically blocked fluorenyl radical was used to build up the first and second generation dendrons <B>FR-G1</B> and <B>FR-G2</B> containing three and seven fluorenyl units, respectively. The neighboring fluorenyl radicals in <B>FR-G1</B> and <B>FR-G2</B> show moderate anti-ferromagnetic exchange interaction, resulting in a doublet and quartet ground state, respectively, with a small doublet–quartet energy gap. From <B>FR-G1</B> to <B>FR-G2</B>, the energy gap decreased and the two-photon absorption was enhanced owing to more extended 2D π-conjugation. Both compounds showed multiple redox waves due to their polyradical character.</P></▼2>
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Fluorenyl Based Macrocyclic Polyradicaloids
Lu, Xuefeng,Lee, Sangsu,Hong, Yongseok,Phan, Hoa,Gopalakrishna, Tullimilli Y.,Herng, Tun Seng,Tanaka, Takayuki,Sandoval-Salinas, Marí,a Eugenia,Zeng, Wangdong,Ding, Jun,Casanova, David,Osuka, At American Chemical Society 2017 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.139 No.37
<P>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.</P>
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