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Pontifical Catholic University of Rio de Janeiro

1. LEONARDO SIMÕES DE ABREU CARNEIRO. [en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION.

Degree: 2016, Pontifical Catholic University of Rio de Janeiro

[pt] Materiais bidimensionais apresentam possibilidades de funcionalização que os tornam versáteis para diversas aplicações, tais como em dispositivos eletrônicos. A presença de poros nesses materiais pode trazer novas funções, como adsorção de gases, liberação controlada de fármacos e catálise. Os covalent organic frameworks (COFs) são uma nova classe de materiais orgânicos porosos cristalinos que têm recebido destaque em química reticular. O objetivo dessa dissertação é apresentar a síntese e caracterização de quatro novos COFs baseados em carbazóis, que constitui uma classe de compostos utilizada na obtenção de polímeros condutores. O bloco de montagem principal utilizado foi o 3,6-diamino-9H-carbazol e as fontes de aldeído foram triformilfloroglucinol, triformilfenol, 1,3,5-tri(4-formilfenil)benzeno e triformilbenzeno para a síntese do RIO2, RIO3, RIO5 e RIO6, respectivamente. RIO2 e RIO3 apresentaram-se sob a forma ceto enamina e imina, respectivamente, além de pouca cristalinidade e baixa área específica. Através de cálculos baseados na Teoria do Funcional da Densidade (DFT), foi verificado que esses COFs apresentam suas folhas deslocadas e rotacionadas devido às interações eletrostáticas e para minimizar os momentos de dipolo das ligações N-H dos carbazóis. RIO5 e RIO6 também se apresentaram pouco cristalinos e com áreas específicas baixas. Apesar desses resultados, esses materiais ainda podem ser aplicados em eletrônica orgânica por apresentarem estrutura química compatível com tal aplicação.

[en] Two-dimensional materials have functionalization possibilities that make them versatile for various applications such as in electronic devices. The presence of pores in these materials can give new features to them, such as gas adsorption, drug delivery and catalysis. The covalent organic frameworks (COFs) are a new class of crystalline porous organic materials that have been prominent in reticular chemistry. The purpose of this work is to present the synthesis and characterization of four new COFs based on carbazoles, which are a class of compounds used to obtain conductive polymers. The main building block used was 3,6-diamine-9H-carbazole with the aldehyde sources were triformylphloroglucinol, triformylphenol, 1,3,5-tri(4 formylphenyl)benzene and triformylbenzene to obtain RIO2, RIO3, RIO5 and RIO6, respectively. RIO2 and RIO3 are in keto-enamine and imine form, respectively, as well as have low crystallinity and low specific area. Calculus based on Density Functional Theory (DFT) found that these COFs present their sheets displaced and rotated due to electrostatic interactions and to minimize the dipole moments of the N-H bonds of carbazoles. In an attempt to avoid the absence of pores, RIO5 and RIO6 materials were synthesized, however these COFs also performed poorly crystalline and with low specific areas. Despite these results, these materials can also be applied in organic electronics by presenting chemical structure compatible with such application.

Advisors/Committee Members: CAMILLA DJENNE BUARQUE MULLER.

Subjects/Keywords: [pt] POROSIDADE; [en] POROSITY; [pt] CARBAZOL; [en] CARBAZOL; [pt] COVALENT ORGANIC FRAMEWORKS; [en] COVALENT ORGANIC FRAMEWORKS; [pt] TAUTOMERIA; [en] TAUTOMERISM; [pt] MATERIAL BIDIMENSIONAL; [en] TWO-DIMENSIONAL MATERIAL

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

CARNEIRO, L. S. D. A. (2016). [en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION. (Thesis). Pontifical Catholic University of Rio de Janeiro. Retrieved from http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=28356

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

CARNEIRO, LEONARDO SIMÕES DE ABREU. “[en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION.” 2016. Thesis, Pontifical Catholic University of Rio de Janeiro. Accessed August 06, 2020. http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=28356.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

CARNEIRO, LEONARDO SIMÕES DE ABREU. “[en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION.” 2016. Web. 06 Aug 2020.

Vancouver:

CARNEIRO LSDA. [en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION. [Internet] [Thesis]. Pontifical Catholic University of Rio de Janeiro; 2016. [cited 2020 Aug 06]. Available from: http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=28356.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

CARNEIRO LSDA. [en] CARBAZOLE-BASED COVALENT ORGANIC FRAMEWORKS: CONCEPTION, SYNTHESIS AND CHARACTERIZATION. [Thesis]. Pontifical Catholic University of Rio de Janeiro; 2016. Available from: http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=28356

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

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