Dual Emission of 2-Amino-4-Methylpyrimidine: A Theoretical Study

Shekhovtsov, N. A.; Vinogradova, Katerina A.; Николаенкова, Елена Б.; Krivopalov, V. P.; Bushuev, Mark B.

doi:10.1134/s0022476620100042

Cited by 3 publications

(2 citation statements)

References 28 publications

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“…Compound 1 features dual-band emission with maxima at 450 and 610 nm. The first band is attributed to conventional fluorescence, while the second one can be the result of excited-state intramolecular proton transfer (ESIPT) or the excited-state charge transfer process. ,, The latter transition appears to be the common process for derivatives containing {NH-Pbt} moieties. ,,, The relative intensity of the bands in 1 negligibly changes in the excitation wavelength range of 250–400 nm (Figure S12, SI). The UV–vis absorption spectrum of compound 5 resembles that for 1 with the exception for a less-pronounced long wavelength band in the former.…”

Section: Results and Discussionmentioning

confidence: 99%

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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There is unceasing interest toward transformations of phosphine derivatives, which are facilitated by transition metals. We report a facile Pd(II)-and Pt(II)-assisted P−C bond cleavage in a luminescent 2-phenylbenzothiazole-based αmethylaminophosphine (PCN, 1). Specifically, reactions between 1 and [M(COD)Cl 2 ] (M = Pd, Pt; COD = cycloocta-1,5-diene) in different solvents (methylene chloride, acetonitrile, pyridine, toluene) resulted in the formation of PPh 2 − , captured either as a bridging ligand in binuclear complexes with a {M 2 (PPh 2 ) 2 } moiety or as an adduct to COD in [Pt 2 (PPh 2 COD) 2 Cl 2 ]. The heterocyclic part transforms to annulated c-CN + species with a 1,2-dihydroquinazoline cycle formed. In the presence of pyridine as a base, annulated form c-CN + destabilizes and undergoes reverse cyclization transforming to deprotonated CN form. Quantum-chemical density functional theory (DFT) calculations predict that a crucial step in the reactions involves proton transfer from the N atom of the amino group of PCN to a neighboring molecule. A combination of high photophysical sensitivity of c-CN + toward its immediate environment and rich structural capabilities in assembling (c-CN) 2 2+ pairs in different crystal packings in a family of phases with the general formula (c-CN) 2 [M 2 (PPh 2 ) 2 Cl 4 ] allows one to fine-tune the luminescence properties of the latter. The results were rationalized as a variation of π−π intercationic spacings, which tunes the degree of excitedstate charge transfer between c-CN + cations. As a result, compounds with relatively short interplanar π−π-separation between the cations show a stronger charge-transfer-mediated bathochromic shift.

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Section: Results and Discussionmentioning

confidence: 99%

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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“…PQ tends to form complexes with protic solvents and dimers in nalkane solvents. The ESDPT in the PQ dimer is a reversible process, in which the dimer structure is restored at temperatures above 40 K, with the fluorescence emission disappearing, and then reappearing after irradiation and cooling to 5 K. In addition, ESDPT behavior has been reported in dimers, such as 4-azabenzimidazole, 3-formyl-7-azaindole [79], 3-methyl-7-azaindole [80], 2-amino-4-methylpyrimidine [81], and 3-hydroxyisoquinoline (3-HIQ) (Figure 9b).…”

Section: Esdpt In Dimermentioning

confidence: 99%

Recent progress on the excited-state multiple proton transfer process in organic molecules

et al. 2022

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In contrast to the widely reported excited-state single proton-transfer, excited-state multiple proton transfer (ESMPT) containing two or more intra-or inter-molecular proton transfers has greatly expanded the research scope of the excited-state proton transfers. In recent decades, ESMPT-active organic molecules have attracted much attention owing to their unique photophysical properties, such as large magnitude Stokes shifts and dual emission. These photophysical properties facilitate the application of the organic molecules in organic solid-state lasers, fluorescent probes and sensors, and molecular switches. Herein, we introduce the fundamentals of the ESMPT and review the recent advances in different types of ESMPTs in organic molecules. Finally, we present our conclusions and the future development prospects of the ESMPT in organic molecules. excited-state multiple proton transfer, hydrogen bond, photoisomerization, organic molecules, photophysical properties

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Excitation wavelength-dependent room-temperature phosphorescence: unusual properties of novel phosphinoamines

Khisamov

Ryadun

Sukhikh

et al. 2021

Mol. Syst. Des. Eng.

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Dual Emission of 2-Amino-4-Methylpyrimidine: A Theoretical Study

Cited by 3 publications

References 28 publications

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Recent progress on the excited-state multiple proton transfer process in organic molecules

Excitation wavelength-dependent room-temperature phosphorescence: unusual properties of novel phosphinoamines

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