Study of mesomorphism behavior and protonation-induced emission of symmetrical benzalazines
•New rod-like and polycatenar benzalazines were synthesized and characterized.•Benzalazines without 2-OH showed thermally reversible protonation-induced emission.•Emission capacity of AIEgens was investigated within the liquid crystalline phase.•Compounds showed emission in solution and solid state...
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| Published in: | Journal of molecular structure Vol. 1312; p. 138571 |
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| Main Authors: | , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier B.V
15-09-2024
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| Abstract | •New rod-like and polycatenar benzalazines were synthesized and characterized.•Benzalazines without 2-OH showed thermally reversible protonation-induced emission.•Emission capacity of AIEgens was investigated within the liquid crystalline phase.•Compounds showed emission in solution and solid state after contact with HCl.
Rod-shaped and polycatenar symmetric benzalazines with protonation-induced emission were synthesized, characterized, and studied for their thermal and optical behavior. Benzalazines lacking hydroxy groups at the ortho position did not show luminescence in the solid state or solution. In the presence of HCl (either in solution or vapor form) these compounds became good emitters. The protonation of azine nitrogen that may hinder the NN bond rotation by intermolecular interactions toward aggregates provided an explanation for the emission characteristics observed. The protonation-induced emission was thermally reversible. A benzalazine derived from 4-alkoxysalicylaldehyde with AIE property was prepared. For this compound with ortho-OH groups, the optical properties were not affected by the presence of acidic media. It exhibited a stable SmC phase characterized by POM, DSC, and XRD. The luminescence capability of the molecular arrangement within the smectic phase was investigated. The intense yellow-green emission in the crystals decreased significantly at the phase transition due to the non-radiative decay that occurs with increasing temperature, and loss of intermolecular H-bonding which prevents molecular rotations in the crystal.
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| AbstractList | •New rod-like and polycatenar benzalazines were synthesized and characterized.•Benzalazines without 2-OH showed thermally reversible protonation-induced emission.•Emission capacity of AIEgens was investigated within the liquid crystalline phase.•Compounds showed emission in solution and solid state after contact with HCl.
Rod-shaped and polycatenar symmetric benzalazines with protonation-induced emission were synthesized, characterized, and studied for their thermal and optical behavior. Benzalazines lacking hydroxy groups at the ortho position did not show luminescence in the solid state or solution. In the presence of HCl (either in solution or vapor form) these compounds became good emitters. The protonation of azine nitrogen that may hinder the NN bond rotation by intermolecular interactions toward aggregates provided an explanation for the emission characteristics observed. The protonation-induced emission was thermally reversible. A benzalazine derived from 4-alkoxysalicylaldehyde with AIE property was prepared. For this compound with ortho-OH groups, the optical properties were not affected by the presence of acidic media. It exhibited a stable SmC phase characterized by POM, DSC, and XRD. The luminescence capability of the molecular arrangement within the smectic phase was investigated. The intense yellow-green emission in the crystals decreased significantly at the phase transition due to the non-radiative decay that occurs with increasing temperature, and loss of intermolecular H-bonding which prevents molecular rotations in the crystal.
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| ArticleNumber | 138571 |
| Author | Santos, Gabriel Franco dos Soares, Rafael Gomes Stadtlober, Carlos H. Eccher, Juliana Cristiano, Rodrigo Vaz, Boniek Gontijo Lima-Junior, Claudio Gabriel Will, Sabrina Felippe Lopes, Bruno Galdino Westphal, Eduard de Araújo, Lidiane Gomes Bechtold, Ivan H. |
| Author_xml | – sequence: 1 givenname: Bruno Galdino orcidid: 0000-0001-5733-005X surname: Lopes fullname: Lopes, Bruno Galdino organization: Departamento de Química, Universidade Federal da Paraíba (UFPB), João Pessoa, PB 58051-900, Brazil – sequence: 2 givenname: Lidiane Gomes orcidid: 0000-0002-0416-8201 surname: de Araújo fullname: de Araújo, Lidiane Gomes organization: Departamento de Química, Universidade Federal da Paraíba (UFPB), João Pessoa, PB 58051-900, Brazil – sequence: 3 givenname: Rafael Gomes surname: Soares fullname: Soares, Rafael Gomes organization: Departamento de Química, Universidade Federal da Paraíba (UFPB), João Pessoa, PB 58051-900, Brazil – sequence: 4 givenname: Claudio Gabriel orcidid: 0000-0001-6570-8999 surname: Lima-Junior fullname: Lima-Junior, Claudio Gabriel organization: Departamento de Química, Universidade Federal da Paraíba (UFPB), João Pessoa, PB 58051-900, Brazil – sequence: 5 givenname: Boniek Gontijo surname: Vaz fullname: Vaz, Boniek Gontijo organization: Instituto de Química, Universidade Federal de Goiás (UFG), Goiânia, GO 74690-900, Brazil – sequence: 6 givenname: Gabriel Franco dos surname: Santos fullname: Santos, Gabriel Franco dos organization: Instituto de Química, Universidade Federal de Goiás (UFG), Goiânia, GO 74690-900, Brazil – sequence: 7 givenname: Sabrina Felippe orcidid: 0009-0003-0792-0790 surname: Will fullname: Will, Sabrina Felippe organization: Departamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil – sequence: 8 givenname: Eduard surname: Westphal fullname: Westphal, Eduard organization: Departamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil – sequence: 9 givenname: Ivan H. surname: Bechtold fullname: Bechtold, Ivan H. organization: Departamento de Física Universidade Federal de Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil – sequence: 10 givenname: Carlos H. orcidid: 0009-0005-6754-5165 surname: Stadtlober fullname: Stadtlober, Carlos H. organization: Departamento de Física Universidade Federal de Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil – sequence: 11 givenname: Juliana surname: Eccher fullname: Eccher, Juliana organization: Departamento de Física Universidade Federal de Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil – sequence: 12 givenname: Rodrigo orcidid: 0000-0002-5044-377X surname: Cristiano fullname: Cristiano, Rodrigo email: rcristiano@quimica.ufpb.br organization: Departamento de Química, Universidade Federal da Paraíba (UFPB), João Pessoa, PB 58051-900, Brazil |
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| Keywords | Benzalazines SmC phase Aggregation-induced emission AIE Liquid crystals Protonation-induced emission |
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| Title | Study of mesomorphism behavior and protonation-induced emission of symmetrical benzalazines |
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