Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

Marco Mellado; Rafaela Sariego-Kluge; Franco Valdés-Navarro; Rodrigo Sánchez-González; Mauricio Fuentealba; Manuel A. Bravo; Luis F. Aguilar

doi:10.1016/j.molstruc.2020.129340

Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

Marco Mellado
, Rafaela Sariego-Kluge
, Franco Valdés-Navarro
, Rodrigo Sánchez-González
, Mauricio Fuentealba
, Manuel A. Bravo
, Luis F. Aguilar

Pontificia Universidad Católica de Valparaíso

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from chalcone (8) with 45% yield. We obtained monocrystals of 9 by slow evaporation of dichloromethane as a solvent. Additionally, we measured the photophysical properties of compound 9, and its absorption wavelength (λ_abs), molar absorption coefficient (ε), excitation wavelength (λ_exc) and emission wavelength (λ_em), as well as Stokes shift (Δλ), increase with increasing solvent polarity. These properties are all related to the stabilization of the excited state by the solvent.

Original language	English
Article number	129340
Journal	Journal of Molecular Structure
Volume	1226
DOIs	https://doi.org/10.1016/j.molstruc.2020.129340
State	Published - 15 Feb 2021
Externally published	Yes

Keywords

2-amino-pyrimidin
Absorption properties
Chalcone
Crystal structure
Emission properties

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10.1016/j.molstruc.2020.129340

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@article{af4bdb4ed75d4cef8c2d6ffe5a630067,

title = "Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine",

abstract = "The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from chalcone (8) with 45\% yield. We obtained monocrystals of 9 by slow evaporation of dichloromethane as a solvent. Additionally, we measured the photophysical properties of compound 9, and its absorption wavelength (λabs), molar absorption coefficient (ε), excitation wavelength (λexc) and emission wavelength (λem), as well as Stokes shift (Δλ), increase with increasing solvent polarity. These properties are all related to the stabilization of the excited state by the solvent.",

keywords = "2-amino-pyrimidin, Absorption properties, Chalcone, Crystal structure, Emission properties",

author = "Marco Mellado and Rafaela Sariego-Kluge and Franco Vald{\'e}s-Navarro and Rodrigo S{\'a}nchez-Gonz{\'a}lez and Mauricio Fuentealba and Bravo, \{Manuel A.\} and Aguilar, \{Luis F.\}",

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year = "2021",

month = feb,

day = "15",

doi = "10.1016/j.molstruc.2020.129340",

language = "English",

volume = "1226",

journal = "Journal of Molecular Structure",

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TY - JOUR

T1 - Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

AU - Mellado, Marco

AU - Sariego-Kluge, Rafaela

AU - Valdés-Navarro, Franco

AU - Sánchez-González, Rodrigo

AU - Fuentealba, Mauricio

AU - Bravo, Manuel A.

AU - Aguilar, Luis F.

PY - 2021/2/15

Y1 - 2021/2/15

N2 - The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from chalcone (8) with 45% yield. We obtained monocrystals of 9 by slow evaporation of dichloromethane as a solvent. Additionally, we measured the photophysical properties of compound 9, and its absorption wavelength (λabs), molar absorption coefficient (ε), excitation wavelength (λexc) and emission wavelength (λem), as well as Stokes shift (Δλ), increase with increasing solvent polarity. These properties are all related to the stabilization of the excited state by the solvent.

AB - The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from chalcone (8) with 45% yield. We obtained monocrystals of 9 by slow evaporation of dichloromethane as a solvent. Additionally, we measured the photophysical properties of compound 9, and its absorption wavelength (λabs), molar absorption coefficient (ε), excitation wavelength (λexc) and emission wavelength (λem), as well as Stokes shift (Δλ), increase with increasing solvent polarity. These properties are all related to the stabilization of the excited state by the solvent.

KW - 2-amino-pyrimidin

KW - Absorption properties

KW - Chalcone

KW - Crystal structure

KW - Emission properties

UR - https://www.scopus.com/pages/publications/85091799618

U2 - 10.1016/j.molstruc.2020.129340

DO - 10.1016/j.molstruc.2020.129340

M3 - Article

AN - SCOPUS:85091799618

SN - 0022-2860

VL - 1226

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 129340

ER -

Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

Abstract

Keywords

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