Synthesis and Physicochemical Characterization of New Polythiophenes Based on Three Different Monomers

Guzmán-Rabadán, Karla Karina; Ramírez-Gómez, Marco Antonio; Güizado-Rodrı́guez, Marisol; Guerrero‐Álvarez, Jorge; Barba, Víctor; Basurto-Pensado, M. A.; Galindo, Rosario; Rodríguez, Mario; Maldonado, José Luis

doi:10.1557/opl.2015.227

Cited by 2 publications

(2 citation statements)

References 35 publications

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“…In previous reports, thiophene and EDOT have been widely used as the research basis for many functional conjugated systems [10,11] . This is mainly due to their good strength in electronic and conjugated structures, which brings good charge mobility to the application of organic field‐effect transistors (OFET) [12–17] . However, there has been little research on the role of D−A−D compounds in acid‐induced color change.…”

Section: Introductionmentioning

confidence: 99%

“…[10,11] This is mainly due to their good strength in electronic and conjugated structures, which brings good charge mobility to the application of organic field-effect transistors (OFET). [12][13][14][15][16][17] However, there has been little research on the role of DÀ AÀ D compounds in acid-induced color change. Molecular chromism refers to a color change that occurs under chemical or physical stimuli.…”

Section: Introductionmentioning

confidence: 99%

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Syntheses, Characterization and Acidochromic Properties of Donor‐Acceptor‐Donor Compounds Based on 2‐Amino‐Pyrimidine

Nie,

Xieraili

2023

ChemistrySelect

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Organic materials with a donor-acceptor-donor (DÀ AÀ D) system of π-conjugation exhibit strong intermolecular interactions. This study reports the acid-induced color-changing properties of two DÀ AÀ D type π-conjugated compounds containing 2-aminopyrimidine. When the 3,4-ethylenedioxythiophene (EDOT) moiety is introduced into the DÀ AÀ D compound as an electron donor and analyzed through UVvisible spectroscopy, fluorescence, and thermal characterization, the compound is found to have a narrow bandgap, good thermal stability, and detection ability. The detection limit for methanesulfonic acid is 1.24 × 10 À 9 mol/L. Density functional theory (DFT) indicates that both the protonated and unprotonated DÀ AÀ D compounds achieve a coplanar geometry. In the acid-induced color change, the protonated AETP, EDOT's C 1 atom, and the C 2 atom of the pyrimidine ring rotate into a head-to-head structure, providing sufficient space for proton and pyrimidine N closure. Additionally, The HOMO and LUMO energy levels of ATP and AETP exhibit a notable difference with the former at 2.127 eV and the latter at 2.039 eV. The protonation of these compounds led to a decrease in molecular orbital energy by approximately 50 %, indicating an enhancement in stability relative to their unprotonated counterparts. This observation has significant implications for the design of molecular structures that are responsive to changes in acid concentration, making it valuable for future studies in the field of acid color-changing compounds. Results and Discussion Characterization of the compoundsDetails of synthesis of 2-amino-4, 6-dithienyl-pyrimidine (ATP) and 2-amino-4, 6-bis (3, 4-ethylenedioxythienyl)pyrimidin (AETP) are shown in Scheme 1. The compounds synthesized in this work, ATP and AETP, are characterized by recording their FT-IR, 1 H NMR, 13 C NMR spectra. Moreover, elemental composition of the compounds were confirmed via[a] P.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Syntheses, Characterization and Acidochromic Properties of Donor‐Acceptor‐Donor Compounds Based on 2‐Amino‐Pyrimidine

Nie,

Xieraili

2023

ChemistrySelect

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Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene

Ramírez-Gómez

Guzmán-Rabadán

González-Juárez

et al. 2017

International Journal of Polymer Science

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The chemical synthesis and physicochemical and luminescent characterizations of polymers based on 3-HT, EDOT, and 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl) bisthiophene (fluorene) or (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl 2-(thiophen-3-yl)acetate (TDR1) are reported. The fluorene unit was bound to the conjugate backbone, while the Disperse Red 1 (DR1) chromophore was present as a pendant group. Characterizations by 1H NMR, FT-IR, DSC-TGA, GPC, UV-vis, cyclic voltammetry, fluorescence quantum yield, excited state lifetime, and two-photon absorption cross-section were carried out. These polymers combined the physicochemical properties of EDOT and 3-HT, such as high electron density, high charge mobility, low oxidation potential, and good processability. The optical properties of these copolymers were highly dependent on the presence of EDOT, the molecular weight, and the regioregularity rather than the presence of the third component (fluorene or TDR1). The good nonlinear absorption and luminescent properties exhibited by these copolymers were exploited to fabricate nanoparticles used as fluorescent tags for the imaging of microstructures.

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Synthesis and Physicochemical Characterization of New Polythiophenes Based on Three Different Monomers

Abstract: The chemical synthesis of the copolymers poly(3-HT-co-EDOT-co-fluorene) and poly(3-HT-co-EDOT

Cited by 2 publications

References 35 publications

Syntheses, Characterization and Acidochromic Properties of Donor‐Acceptor‐Donor Compounds Based on 2‐Amino‐Pyrimidine

Syntheses, Characterization and Acidochromic Properties of Donor‐Acceptor‐Donor Compounds Based on 2‐Amino‐Pyrimidine

Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene

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