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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Solvent-Free Synthesis Using Nb2O5 and a Theoretical-Experimental Study of Solvent Effect in New Rhodamine Dyes

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Author(s):
Sacoman Torquato da Silva, Bruno Henrique [1] ; Riehl, Luiza Olbera [2] ; dos Santos, Giovanny Carvalho [2] ; Roldao, Juan Carlos [2] ; da Silva-Filho, Luiz Carlos [2]
Total Authors: 5
Affiliation:
[1] Fed Univ Uberlandia UFU, Chem Inst, BR-38408144 Uberlandia, MG - Brazil
[2] Sao Paulo State Univ UNESP, Sch Sci, Dept Chem, BR-17033360 Bauru, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: CHEMISTRYSELECT; v. 5, n. 4, p. 1455-1463, JAN 31 2020.
Web of Science Citations: 0
Abstract

Rhodamine dyes have several applications based on properties, such as high molar absorptivity, high fluorescence quantum yield, photostability, absorption and emission wavelengths in the visible region. In this paper, we describe the solvent-free synthesis of rhodamines between m-aminophenol derivatives (3-dimethylamino and 3-diethylaminophenol) and phthalic anhydride derivatives (with and without halogens in the benzene ring) using Nb2O5 as catalyst. The compounds were produced in high yields (79 to 90%) within one hour of reaction time and with catalyst recovery. Additionally, a solvatochromic study of rhodamine derivatives was described. These compounds have absorption and emission bands at wavelengths in the visible region and a high quantum yield that potentially makes them good dyes for use in electronic devices (e. g. lasers, OLEDs). The DFT calculations provided a basis for understanding the effect of the solvent on the structural forms of rhodamine and corroborated with the experimental data, where the zwitterionic form is predominant in polar solvents, while in apolar solvents the lactonic form is the most stable. (AU)

FAPESP's process: 14/01337-1 - Studies about the use of Niobium pentachloride, as Lewis acid, in Friedel Crafts acylation reactions, aiming the synthesis of compounds with potential application as sensitized dyes in organic eletronic devices.
Grantee:Bruno Henrique Sacoman Torquato da Silva
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 16/01599-1 - Studies about the use of NbCl5 in multicomponent reactions for the synthesis of organic dyes
Grantee:Luiz Carlos da Silva Filho
Support type: Regular Research Grants
FAPESP's process: 15/00615-0 - Studies on the synthesis and photochemical and photophysical characterization of quinoline derivatives with donor-p-acceptor structure for use as sensitizing dyes in organic electronic devices
Grantee:Giovanny Carvalho dos Santos
Support type: Scholarships in Brazil - Doctorate