The ubiquity and structural and functional diversity of anions continue to call for receptors that can differentiate, sense, and sequester anions selectively. Since majority of the existing anion receptors rely on hydrogen bonding and Coulombic attraction�interactions that normalize the electronic properties of anions�they can only distinguish anions on the basis of their size and shapes rather than their electronic properties. Furthermore, because of the nonchromogenic nature of these interactions, additional signaling units are needed for the sensing of guest anions.In this talk, I will show that depending on the electron-donating capacity of anions and electron-accepting abilities of p-acidic receptors, such as naphthalenediimide and perylenediimide, they can participate in electron transfer (ET) and charge transfer (CT) processes as well as anion�p and CH���anion interactions.1�3 In aprotic solvents, strong Lewis basic anions, such as hydroxide and fluoride trigger ET to NDI and PDI derivatives generating the corresponding radical anions and dianions; less basic anions, such as iodide and bromide produce CT complexes; and charge-diffuse anions, such as triflate and perchlorate form anion�p and CH���anion contacts. While the chromogenic ET and CT events offer a brand new anion sensing method, nonchromogenic anion�p and CH���anion interactions can promote the formation of noncatenated metal�organic frameworks that can capture large, charge-diffuse anions within their cavities. Different modes of anion/p-acid interactions can be utilized not only for the advancement of anion recognition chemistry, but also for the development of new functional materials.Reference:1. Guha, S.; Goodson, F. S.; Corson, L. J.; Saha, S. JACS 2012  , 134, 13679.2. Goodson, F. S.; Panda, D. K.; Ray, S.; Mitra, A.; Guha, S.; Saha, S. OrgBiomolChem 2013  , 11, 4797.3. Mitra, A.; Hubley, C. T.; Panda, D. K.; Clark, R. J.; Saha, S. ChemCommun 2013  , 49, 6629.

Anion sensing through electron transfer and charge transfer events

248th National Meeting (2014)

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