Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices

José A. Sánchez-Fernández, Laura Peña-Parás, Román Vidaltamayo, Andrea Cárdenas-Romero, Gilberto E. García-Acosta

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

This work describes the chemical synthesis, physical analysis, and spectroscopic studies of new chromophores for the obtainment of functionalized high-performance polymers with nonlinear optical properties. Various criteria were considered in order to design these chromophores. First, diphenolic isomers were obtained: dipropargyl-oxy-benzoyl-{2-[4-(4- Nitrophenylaze)-N-ethyl-phenylamino]ethoxy}. To promote the formation of esters, several measures were taken to protect the carboxyl groups including the formation of methilic esters to avoid the formation of high quantities of water-soluble substances and avoid the formation of propargyl ester during the reaction of phenolic hydroxyl groups in all isomers of the dihydroxybenzoic acid, given that propargyl groups are not needed during basic hydrolysis. Because of this, the formation of esters on dihydroxybenzoic acid with the photon-emitting 2,5-dimethylphenacyl and the hydrazone of the benzophenone were evaluated. Next, dihydroxy-oxybenzoil-(9H-carbazole-9- ethoxy) was obtained through the direct reaction of the isomers in dihydroxybenzoic acid with 9H-carbazole-9-ethanol in presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine (TPP).

Original languageEnglish
Title of host publicationAES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications
PublisherAdvanced Engineering Solutions
Pages167-172
Number of pages6
VolumePart F124384
Publication statusPublished - 1 Jan 2016
EventAES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications -
Duration: 1 Jan 2016 → …

Conference

ConferenceAES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications
Period1/1/16 → …

Fingerprint

Azobenzene
Chromophores
Energy storage
Esters
Optical properties
Isomers
Electrons
Acids
Hydrazones
Hydroxyl Radical
Hydrolysis
Polymers
Ethanol
Photons
carbazole
azobenzene
Water

All Science Journal Classification (ASJC) codes

  • Mechanics of Materials
  • Materials Science(all)

Cite this

Sánchez-Fernández, J. A., Peña-Parás, L., Vidaltamayo, R., Cárdenas-Romero, A., & García-Acosta, G. E. (2016). Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices. In AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications (Vol. Part F124384, pp. 167-172). Advanced Engineering Solutions.
Sánchez-Fernández, José A. ; Peña-Parás, Laura ; Vidaltamayo, Román ; Cárdenas-Romero, Andrea ; García-Acosta, Gilberto E. / Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices. AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications. Vol. Part F124384 Advanced Engineering Solutions, 2016. pp. 167-172
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abstract = "This work describes the chemical synthesis, physical analysis, and spectroscopic studies of new chromophores for the obtainment of functionalized high-performance polymers with nonlinear optical properties. Various criteria were considered in order to design these chromophores. First, diphenolic isomers were obtained: dipropargyl-oxy-benzoyl-{2-[4-(4- Nitrophenylaze)-N-ethyl-phenylamino]ethoxy}. To promote the formation of esters, several measures were taken to protect the carboxyl groups including the formation of methilic esters to avoid the formation of high quantities of water-soluble substances and avoid the formation of propargyl ester during the reaction of phenolic hydroxyl groups in all isomers of the dihydroxybenzoic acid, given that propargyl groups are not needed during basic hydrolysis. Because of this, the formation of esters on dihydroxybenzoic acid with the photon-emitting 2,5-dimethylphenacyl and the hydrazone of the benzophenone were evaluated. Next, dihydroxy-oxybenzoil-(9H-carbazole-9- ethoxy) was obtained through the direct reaction of the isomers in dihydroxybenzoic acid with 9H-carbazole-9-ethanol in presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine (TPP).",
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Sánchez-Fernández, JA, Peña-Parás, L, Vidaltamayo, R, Cárdenas-Romero, A & García-Acosta, GE 2016, Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices. in AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications. vol. Part F124384, Advanced Engineering Solutions, pp. 167-172, AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications, 1/1/16.

Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices. / Sánchez-Fernández, José A.; Peña-Parás, Laura; Vidaltamayo, Román; Cárdenas-Romero, Andrea; García-Acosta, Gilberto E.

AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications. Vol. Part F124384 Advanced Engineering Solutions, 2016. p. 167-172.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

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N2 - This work describes the chemical synthesis, physical analysis, and spectroscopic studies of new chromophores for the obtainment of functionalized high-performance polymers with nonlinear optical properties. Various criteria were considered in order to design these chromophores. First, diphenolic isomers were obtained: dipropargyl-oxy-benzoyl-{2-[4-(4- Nitrophenylaze)-N-ethyl-phenylamino]ethoxy}. To promote the formation of esters, several measures were taken to protect the carboxyl groups including the formation of methilic esters to avoid the formation of high quantities of water-soluble substances and avoid the formation of propargyl ester during the reaction of phenolic hydroxyl groups in all isomers of the dihydroxybenzoic acid, given that propargyl groups are not needed during basic hydrolysis. Because of this, the formation of esters on dihydroxybenzoic acid with the photon-emitting 2,5-dimethylphenacyl and the hydrazone of the benzophenone were evaluated. Next, dihydroxy-oxybenzoil-(9H-carbazole-9- ethoxy) was obtained through the direct reaction of the isomers in dihydroxybenzoic acid with 9H-carbazole-9-ethanol in presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine (TPP).

AB - This work describes the chemical synthesis, physical analysis, and spectroscopic studies of new chromophores for the obtainment of functionalized high-performance polymers with nonlinear optical properties. Various criteria were considered in order to design these chromophores. First, diphenolic isomers were obtained: dipropargyl-oxy-benzoyl-{2-[4-(4- Nitrophenylaze)-N-ethyl-phenylamino]ethoxy}. To promote the formation of esters, several measures were taken to protect the carboxyl groups including the formation of methilic esters to avoid the formation of high quantities of water-soluble substances and avoid the formation of propargyl ester during the reaction of phenolic hydroxyl groups in all isomers of the dihydroxybenzoic acid, given that propargyl groups are not needed during basic hydrolysis. Because of this, the formation of esters on dihydroxybenzoic acid with the photon-emitting 2,5-dimethylphenacyl and the hydrazone of the benzophenone were evaluated. Next, dihydroxy-oxybenzoil-(9H-carbazole-9- ethoxy) was obtained through the direct reaction of the isomers in dihydroxybenzoic acid with 9H-carbazole-9-ethanol in presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine (TPP).

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Sánchez-Fernández JA, Peña-Parás L, Vidaltamayo R, Cárdenas-Romero A, García-Acosta GE. Synthesis of chromophores based on carbazole & azobenzenes as electron donors & acceptors with nonlinear optoelectrical & optical properties & applications in energy storage devices. In AES-ATEMA International Conference Series - Advances and Trends in Engineering Materials and their Applications. Vol. Part F124384. Advanced Engineering Solutions. 2016. p. 167-172