New polyimides containing methyl benzamidobenzoate or dimethyl benzamidoisophthalate as bulky pendant groups. Effects on solubility, thermal and gas transport properties
Claudio A. Terraza
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
UC Energy Research Center, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Conceptualization (equal), Data curation (equal)
Search for more papers by this authorYennier Cruz
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal), Writing - original draft (equal)
Search for more papers by this authorAry Rodríguez
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorMaría Victoria Velázquez-Tundidor
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorRené A. Hauyon
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Writing - review & editing (equal)
Search for more papers by this authorFidel E. Rodríguez-González
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorVladimir Niebla
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorManuel Aguilar-Vega
Unidad de Materiales, Laboratorio de Membranas, Centro de Investigación Científica de Yucatán A.C, Mérida, Mexico
Contribution: Supervision (equal)
Search for more papers by this authorRita Sulub-Sulub
Unidad de Materiales, Laboratorio de Membranas, Centro de Investigación Científica de Yucatán A.C, Mérida, Mexico
Contribution: Data curation (equal)
Search for more papers by this authorDeysma Coll
Centro de Nanotecnología Aplicada y Núcleo de Química y Bioquímica, Facultad de Ciencias, Ingeniería y Tecnología. Universidad Mayor, Santiago, Chile
Contribution: Supervision (equal), Writing - original draft (equal)
Search for more papers by this authorPablo A. Ortiz
Centro de Nanotecnología Aplicada, Facultad de Ciencias, Ingeniería y Tecnología, Universidad Mayor, Santiago, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorYasmín P. Pérez
Laboratory of Organic and Polymeric Materials, Faculty of Sciences, Department of Chemistry, Universidad de Tarapacá, Arica, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorCorresponding Author
Bibiana Comesaña-Gándara
Institute of Sustainable Processes, University of Valladolid, Valladolid, Spain
Correspondence
Alain Tundidor-Camba, Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile.
Email: [email protected]
Bibiana Comesaña-Gándara, Institute of Sustainable Processes, University of Valladolid, Dr. Mergelina, s/n, 47011, Valladolid, Spain.
Email: [email protected]
Search for more papers by this authorCorresponding Author
Alain Tundidor-Camba
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
UC Energy Research Center, Pontificia Universidad Católica de Chile, Santiago, Chile
Correspondence
Alain Tundidor-Camba, Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile.
Email: [email protected]
Bibiana Comesaña-Gándara, Institute of Sustainable Processes, University of Valladolid, Dr. Mergelina, s/n, 47011, Valladolid, Spain.
Email: [email protected]
Contribution: Conceptualization (lead), Methodology (lead), Resources (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorClaudio A. Terraza
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
UC Energy Research Center, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Conceptualization (equal), Data curation (equal)
Search for more papers by this authorYennier Cruz
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal), Writing - original draft (equal)
Search for more papers by this authorAry Rodríguez
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorMaría Victoria Velázquez-Tundidor
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorRené A. Hauyon
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Writing - review & editing (equal)
Search for more papers by this authorFidel E. Rodríguez-González
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorVladimir Niebla
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
Contribution: Investigation (equal)
Search for more papers by this authorManuel Aguilar-Vega
Unidad de Materiales, Laboratorio de Membranas, Centro de Investigación Científica de Yucatán A.C, Mérida, Mexico
Contribution: Supervision (equal)
Search for more papers by this authorRita Sulub-Sulub
Unidad de Materiales, Laboratorio de Membranas, Centro de Investigación Científica de Yucatán A.C, Mérida, Mexico
Contribution: Data curation (equal)
Search for more papers by this authorDeysma Coll
Centro de Nanotecnología Aplicada y Núcleo de Química y Bioquímica, Facultad de Ciencias, Ingeniería y Tecnología. Universidad Mayor, Santiago, Chile
Contribution: Supervision (equal), Writing - original draft (equal)
Search for more papers by this authorPablo A. Ortiz
Centro de Nanotecnología Aplicada, Facultad de Ciencias, Ingeniería y Tecnología, Universidad Mayor, Santiago, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorYasmín P. Pérez
Laboratory of Organic and Polymeric Materials, Faculty of Sciences, Department of Chemistry, Universidad de Tarapacá, Arica, Chile
Contribution: Formal analysis (equal)
Search for more papers by this authorCorresponding Author
Bibiana Comesaña-Gándara
Institute of Sustainable Processes, University of Valladolid, Valladolid, Spain
Correspondence
Alain Tundidor-Camba, Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile.
Email: [email protected]
Bibiana Comesaña-Gándara, Institute of Sustainable Processes, University of Valladolid, Dr. Mergelina, s/n, 47011, Valladolid, Spain.
Email: [email protected]
Search for more papers by this authorCorresponding Author
Alain Tundidor-Camba
Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile
UC Energy Research Center, Pontificia Universidad Católica de Chile, Santiago, Chile
Correspondence
Alain Tundidor-Camba, Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Católica de Chile, Santiago, Chile.
Email: [email protected]
Bibiana Comesaña-Gándara, Institute of Sustainable Processes, University of Valladolid, Dr. Mergelina, s/n, 47011, Valladolid, Spain.
Email: [email protected]
Contribution: Conceptualization (lead), Methodology (lead), Resources (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorFunding information: Agencia Nacional de Investigación y Desarrollo (ANID), Grant/Award Number: 1190772
Abstract
This work reports the synthesis of six new polyimides obtained by the reaction of two novel diamine monomers: methyl 4-(3,5-diaminobenzamido)benzoate and dimethyl 5-(3,5-diaminobenzamido)isophthalate, bearing one or two methyl ester groups in their phenyl rings, respectively, with three known dianhydrides, 4,4′-(hexafluoroisopropylidene) diphatalic anhydride (6FDA), 4,4′-(dimethylsilanediyl) dipthalic anhydride (SiDA) and 4,4′-oxydiphthalic anhydride (ODPA). The polyimides were synthesized using the “two-step” method, which first involves forming a poly(amic acid) precursor that is subsequently cyclodehydrated to form the imide linkage. The yields were higher than 95% in all cases, and the structural characterization was performed by spectroscopic techniques like FT-IR, 1H, 13C, and 29Si NMR. In addition, the effect on the solubility in common organic solvents and thermal and gas transport properties of these polyimides were studied as a function of the nature of the respective side group and the dianhydride used.
CONFLICT OF INTEREST
The authors declare no conflicts of interest.
Open Research
DATA AVAILABILITY STATEMENT
The raw data required to reproduce these findings are included in the article. Research data are not shared.
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