Solvent-controlled tautomerism of malononitrile-naphthalimide via intramolecular proton transfer

Lan, Haichuang; Li, Qian; Li, Yang; Xiao, Shuzhang; Li, Yaqian; Yan, Xufeng; Yuan, Shuang; Zhu, Pengcheng

doi:10.1016/j.dyepig.2018.03.031

Cited by 9 publications

(2 citation statements)

References 26 publications

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“…Prototropic tautomerism, intramolecular transfer of hydrogen from one atom to another, is a common phenomenon in living systems. − Keto–enol tautomerism is a typical paradigm of intramolecular proton transfer, and it is of great significance in biochemistry. − The canonical keto form and its corresponding rare tautomeric enol form of the bases guanine and thymine exist in cells, and the tautomerism of base pairs which have different base-pairing properties increases the uncertainty of genetic information, resulting in an imprecision of the recognition, replication, and transfer of genetic information . Essentially, an intrinsic genetic instability arisen by keto–enol tautomerism in cells possibly facilitates mutation and even cancer development. − Therefore, it is extraordinarily important to study how to control keto–enol tautomerism.…”

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confidence: 99%

Controlling Keto–Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array

Zhang

et al. 2020

Org. Lett.

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Units of ureidopyrimidinone (UPy) which dimerize via strong quadruple hydrogen bonding are widely used for the construction of supramolecular systems. This self-complementary system exists in the tautomerism equilibrium of 4[1H]-pyrimidinone dimer and pyrimidin-4-ol dimer, making generated supramolecular assembly systems essentially complicated. In this contribution, a rational but simple design concept is described for preorganizing the self-complementary quadruple hydrogen bonding of UPy via supramolecular strategy into a single-quadruple DDAA-AADD dimeric array. With this concept, the designed UPy derivatives form only 4[1H]-pyrimidinone dimer with a ketone configuration via intermolecular hydrogen-bonding interactions, both in the solid state as well as in solution, as is evident from single-crystal X-ray diffraction and 1H NMR spectroscopy. The single DDAA-AADD dimeric array provides defined noncovalent driving forces that can be used to generate constitutionally clear supramolecular structures that are vitally important in the fields of supramolecular chemistry and materials.

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confidence: 99%

Controlling Keto–Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array

Zhang

et al. 2020

Org. Lett.

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“…The theoretical calculations, using explicit solvation in MeOH, demonstrate that the specific intermolecular interactions of the solvent with the CO group in the keto forms are much stronger (Table S1), which explains the experimentally observed K2QH stabilization. It is worth mentioning that tautomeric systems displaying solvent triggered long-range proton transfer behavior are quite rare , and their proton-switched single-crystal X-ray structure analysis has never been reported until now. For the ground enol/keto short-range intramolecular proton transfer (via six-membered hydrogen bonding), empirical and theoretical data exert an influence, − but the mechanism of long-range proton transport remains unclear.…”

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confidence: 99%

Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group

et al. 2022

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The ability of long-range proton transport by substitution of 7-hydroxyquinoline at the eighth position with sulfonamide and sulfonylhydrazone rotor units to act as a cranearm has been studied. Different proton transport pathways triggered by different stimuli have been established depending on the structure of the crane-arms. Solvent-driven proton switching from OH to the quinoline nitrogen (N quin ) site, facilitated by a sulfonamide transporter group in polar protic and aprotic solvents, has been confirmed by optical (absorption and fluorescence) and NMR spectroscopies as well as by single-crystal X-ray structure analysis. Photoinduced long-range proton transport to the N quin site upon 340 nm UV light irradiation has been estimated in sulfonylhydrazone, which is not sensitive to solvent-driven switching. Both compounds have exhibited acid-triggered switching by trifluoroacetic acid due to the formation of a stable six-membered intramolecular hydrogen bonding interaction between the protonated N quin and crane-arm. The structures of acid-switched form were confirmed by NMR spectroscopy and single-crystal X-ray structure analysis. The behavior of the compounds suggests a big step forward in the advanced proton pump-switching architecture because they cover three distinct driving forces in the switching process: solvent, light, and acid.

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Synthesis and Investigation of Derivatives of 1,8-Naphthalimide with a Red Emission via an Aromatic Nucleophilic Substitution Reaction

et al. 2022

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Solvent-controlled tautomerism of malononitrile-naphthalimide via intramolecular proton transfer

Cited by 9 publications

References 26 publications

Controlling Keto–Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array

Controlling Keto–Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array

Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group

Synthesis and Investigation of Derivatives of 1,8-Naphthalimide with a Red Emission via an Aromatic Nucleophilic Substitution Reaction

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