The first electronically stabilized phenalenyl radical: Effect of substituents on solution chemistry and solid-state structure

Beer L; Mandal SK; Reed RW; Oakley RT; Tham FS; Donnadieu B; Haddon RC

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The first electronically stabilized phenalenyl radical: Effect of substituents on solution chemistry and solid-state structure

机译：第一个电子稳定的菲基：取代基对溶液化学和固态结构的影响

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We report an investigation into the effect of oxygen and sulfur substitution on the dimerization of phenalenyl-based neutral radicals; these substituents are expected to electronically stabilize the free radical while sterically interfering with dimerization. The 1,3,4,9-tetramethoxyphenalenyl (7a) and 1-ethoxy-3,4,9-trimethoxyphenalenyl (7b) radicals are prepared by chemical reduction of the cation salts, but the crystals that are isolated from these solutions are shown to be composed of alkoxy-substituted peropyrenes by X-ray crystallography. Crystallization of 1,9-dithiophenalenyl (8) gives rise to a pi-dimer, and this is the first example of a radical based on a single phenalenyl unit that has been stabilized against sigma-dimerization in the solid state by electronic effects rather than by the presence of sterically bulky substituents.

机译：我们报告了对氧和硫取代对基于菲基的中性自由基二聚化的影响的研究;这些取代基有望在空间上干扰二聚作用的同时电子稳定自由基。 1,3,4,9-四甲氧基苯基（7a）和1-乙氧基-3,4,9-三甲氧基苯基（7b）自由基是通过阳离子盐的化学还原制备的，但显示了从这些溶液中分离出的晶体通过X射线晶体学分析由烷氧基取代的过氧化戊烯组成。 1,9-二噻吩基烯基（8）的结晶会生成pi-二聚体，这是基于单个酚基单元的自由基的第一个实例，该基团已通过电子作用而不是固态作用稳定了固态的σ-二聚作用由于存在空间大的取代基。

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《Crystal growth & design》 |2007年第4期|共8页
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Beer L; Mandal SK; Reed RW; Oakley RT; Tham FS; Donnadieu B; Haddon RC;
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正文语种 eng
中图分类晶体学;
关键词
BOND GROUND-STATE; MOLECULAR CONDUCTORS; ORGANIC METALS; PHYSICAL-PROPERTIES; DESIGN; CRYSTAL; SYSTEM; DIMER; TETRATHIAFULVALENE; POLYMERS;

机译：键基态;分子导体;有机金属;物理性质;设计;晶体;体系;二聚体;四硫代富勒烯;聚合物;

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1. The first electronically stabilized phenalenyl radical: Effect of substituents on solution chemistry and solid-state structure [J] . Beer L, Mandal SK, Reed RW, Crystal growth & design . 2007,第4期

机译：第一个电子稳定的菲基：取代基对溶液化学和固态结构的影响
2. Curve-structured Phenalenyl Chemistry: Synthesis, Electronic Structure, And Bowl-inversion Barrier Of A Phenalenyl-fused Corannulene Anion [J] . Shinsuke Nishida, Yasushi Morita, Akira Ueda, Journal of the American Chemical Society . 2008,第45期

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3. ESR and calculations on electronic structure of phenalenyl and phenalenyl derivative radicals [J] . Piccinato Marilene Turini, da Costa Marcello Ferreira, Ota Andre Tsutomu, Magnetic Resonance in Chemistry: MRC . 2015,第2期

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5. Multicenter covalent pi -pi bonding interaction and its role in the solid-state properties of phenalenyl-based organic radical materials [D] . Huang, Jingsong. 2006

机译：多中心共价PI -PI键合相互作用及其在苯甲基有机基质固态性质中的作用
6. A new face of phenalenyl-based radicals in the transition metal-free C–H arylation of heteroarenes at room temperature: trapping the radical initiator via C–C σ-bond formation [O] . Jasimuddin Ahmed, Sreejyothi P, Gonela Vijaykumar, 2017

机译：室温下杂芳烃的无过渡金属CH–H芳基化中基于苯二烯基的自由基的新面貌：通过C–Cσ键形成捕获自由基引发剂
7. The First Electronically Stabilized Phenalenyl Radical: Effect of Substituents on Solution Chemistry and Solid-State Structure [O] . -1

机译：第一电子稳定的酚基团：取代基对溶液化学和固态结构的影响

The first electronically stabilized phenalenyl radical: Effect of substituents on solution chemistry and solid-state structure

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