Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1 `-(2 `-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives
Por:
Villa-Martinez, Cesar A., Magana-Vergara, Nancy E., Rodriguez, Mario, Mojica-Sanchez, Juan P., Ramos-Organillo, Angel A., Barroso-Flores, Joaquin, Padilla-Martinez, Itzia I., Martinez-Martinez, Francisco J.
Publicada:
1 jun 2022
Resumen:
Intramolecular charge transfer (ICT) effects are responsible for the
photoluminescent properties of coumarins. Hence, optical properties with
different applications can be obtained by ICT modulation. Herein, four
3-acetyl-2H-chromen-2-ones (1a-d) and their corresponding fluorescent
hybrids 3- (phenylhydrazone)-chromen-2-ones (2a-d) were synthesized in
74-65% yields. The UV-Vis data were in the 295-428 nm range. The
emission depends on the substituent in position C-7 bearing
electron-donating groups. Compounds 1b-d showed good optical properties
due to the D-pi-A structural arrangement. In compounds 2a-d, there is a
quenching effect of fluorescence in solution. However, in the solid, an
increase is shown due to an aggregation-induced emission (AIE) effect
given by the rotational restraints and stacking in the crystal.
Computational calculations of the HOMO-LUMO orbitals indicate high
absorbance and emission values of the molecules, and gap values
represent the bathochromic effect and the electronic efficiency of the
compounds. Compounds 1a-d and 2a-d are good candidates for optical
applications, such as OLEDs, organic solar cells, or fluorescence
markers.
Filiaciones:
Villa-Martinez, Cesar A.:
Univ Colima, Fac Ciencias Quim, Km 9 Carretera Coquimatlan Colima, Coquimatlan 28400, Mexico
Magana-Vergara, Nancy E.:
Univ Colima, Fac Ciencias Quim, CONACyT, Km 9 Carretera Coquimatlan Colima, Coquimatlan 28400, Mexico
Rodriguez, Mario:
Ctr Invest Opt, AP 1-948, Leon 37000, Mexico
Mojica-Sanchez, Juan P.:
Inst Tecnol Jose Mario Molina Pasquel & Henr, Tecnol Nacl Mexico, Campus Tamazula Gordiano,Tamazula Santa Rosa 329, Tamazula de Gordiano 49650, Mexico
Ramos-Organillo, Angel A.:
Univ Colima, Fac Ciencias Quim, Km 9 Carretera Coquimatlan Colima, Coquimatlan 28400, Mexico
Barroso-Flores, Joaquin:
UAEM UNAM, Ctr Conjunto Invest Quim Sustentable, Unidad San Cayetano, Carretera Toluca Atlacomulco Km 14 5, Toluca de Lerdo 50200, Mexico
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Padilla-Martinez, Itzia I.:
Inst Politecn Nacl, UPIBI, Lab Quim Supramol & Nanociencias, Av Acueducto sn Barrio Laguna Ticoman, Ciudad de Mexico 07340, Mexico
Martinez-Martinez, Francisco J.:
Univ Colima, Fac Ciencias Quim, Km 9 Carretera Coquimatlan Colima, Coquimatlan 28400, Mexico
Green Published, gold, Gold, Green
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