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- W2313367246 abstract "Stabilization of radical ions and highly electron-deficient systems under ambient conditions is of great significance. A new design concept is presented that applies the multifaceted features of the phosphonium group to achieve isolation of (a) the first naphthalenediimide (NDI) radical ion [(1a•+)BPh4(–)] as single crystals and (b) an ultra-electron-deficient NDI [(1a(2+))2BF4(–)] having the lowest LUMO level recorded for an NDI, overwhelming the formative tetracyanoquinodimethane (TCNQ) molecule. Both 1a•+ and 1a(2+) exhibit unprecedented stability to normal workup procedures, chromatography, and anion metathesis in open air. To our knowledge, this is the first instance where radical ions stable toward chromatography have been obtained, which is a noteworthy development in the field of synthetic radical chemistry. The crucial components of thermodynamic and kinetic stabilization, namely, the nonbonded P···O interaction, hypervalency, and propeller-like shape of the phosphonium groups in 1a(2+) and 1a•+, were substantiated by crystallography and theoretical studies. Natural bond orbital (NBO) calculations validated the P···O contact to be an nO → σP–C* orbital interaction. Spontaneous electron transfer reactions of 1a(2+) even in nonpolar solvents, anion−π interactions of 1a(2+) with the naphthalene core, and panchromism of 1a•+ are the other emergent properties. The high-yielding (∼90%) in situ synthesis of 1a•+ and the extraordinary stability fostered by the phosphonium group have the potential to turn hitherto unstable organic systems into a new genre of stable off-the-shelf systems." @default.
- W2313367246 created "2016-06-24" @default.
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- W2313367246 date "2014-08-13" @default.
- W2313367246 modified "2023-10-17" @default.
- W2313367246 title "Extraordinary Stability of Naphthalenediimide Radical Ion and Its Ultra-Electron-Deficient Precursor: Strategic Role of the Phosphonium Group" @default.
- W2313367246 cites W1965005132 @default.
- W2313367246 cites W1966013891 @default.
- W2313367246 cites W1968629160 @default.
- W2313367246 cites W1969697060 @default.
- W2313367246 cites W1974404779 @default.
- W2313367246 cites W1976218969 @default.
- W2313367246 cites W1980607865 @default.
- W2313367246 cites W1998887217 @default.
- W2313367246 cites W1999043089 @default.
- W2313367246 cites W2000759897 @default.
- W2313367246 cites W2002138370 @default.
- W2313367246 cites W2008551156 @default.
- W2313367246 cites W2009195167 @default.
- W2313367246 cites W2009680181 @default.
- W2313367246 cites W2011720671 @default.
- W2313367246 cites W2012770834 @default.
- W2313367246 cites W2013238362 @default.
- W2313367246 cites W2013800619 @default.
- W2313367246 cites W2014166091 @default.
- W2313367246 cites W2014200671 @default.
- W2313367246 cites W2020042245 @default.
- W2313367246 cites W2021573277 @default.
- W2313367246 cites W2030265138 @default.
- W2313367246 cites W2044402768 @default.
- W2313367246 cites W2047826834 @default.
- W2313367246 cites W2051289111 @default.
- W2313367246 cites W2060333702 @default.
- W2313367246 cites W2063170663 @default.
- W2313367246 cites W2066956355 @default.
- W2313367246 cites W2067423791 @default.
- W2313367246 cites W2079486099 @default.
- W2313367246 cites W2079723858 @default.
- W2313367246 cites W2081504104 @default.
- W2313367246 cites W2082911375 @default.
- W2313367246 cites W2084424275 @default.
- W2313367246 cites W2088133898 @default.
- W2313367246 cites W2090513161 @default.
- W2313367246 cites W2092024458 @default.
- W2313367246 cites W2092417410 @default.
- W2313367246 cites W2096345901 @default.
- W2313367246 cites W2101076261 @default.
- W2313367246 cites W2102642661 @default.
- W2313367246 cites W2104735837 @default.
- W2313367246 cites W2106431371 @default.
- W2313367246 cites W2117569373 @default.
- W2313367246 cites W2121715335 @default.
- W2313367246 cites W2122185004 @default.
- W2313367246 cites W2123469142 @default.
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- W2313367246 cites W2142791660 @default.
- W2313367246 cites W2154633398 @default.
- W2313367246 cites W2157074179 @default.
- W2313367246 cites W2164839953 @default.
- W2313367246 cites W2172920303 @default.
- W2313367246 cites W2316444823 @default.
- W2313367246 cites W2319311343 @default.
- W2313367246 cites W2320188308 @default.
- W2313367246 cites W2320233858 @default.
- W2313367246 cites W2320434952 @default.
- W2313367246 cites W2323940841 @default.
- W2313367246 cites W2325901074 @default.
- W2313367246 cites W2327280959 @default.
- W2313367246 cites W2333381872 @default.
- W2313367246 cites W264642757 @default.
- W2313367246 cites W4256529027 @default.
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- W2313367246 doi "https://doi.org/10.1021/ja504903j" @default.
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