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Doctoral Thesis
DOI
10.11606/T.46.2012.tde-05092012-100130
Document
Author
Full name
Bernardo Almeida Iglesias
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2012
Supervisor
Committee
Araki, Koiti (President)
Angnes, Lucio
Azzellini, Gianluca Camillo
Iamamoto, Yassuko
Winnischofer, Herbert
Title in Portuguese
Síntese e propriedades espectroscópicas e eletroquímicas de uma triazeno-porfirina
Keywords in Portuguese
Compostos heterocíclicos
Porfirinas
Síntese de porfirinas
Sistemas doador- receptor
Transferência de carga
Triazeno-porfirinas
Triazenos
Abstract in Portuguese
Nesta tese foi desenvolvida uma nova classe de porfirinas supramoleculares contendo um grupo (4-nitrofenil)triazeno ligado na posição meso-aril do anel porfirínico. Suas propriedades estruturais e eletrônicas foram investigadas por espectrometria de massas, espectroscopia eletrônica de absorção e emissão, cálculos teóricos semi-empíricos, ressonância magnética nuclear de 1H e 13C, voltametria cíclica e espectroeletroquímica. Efeitos eletrônicos e estruturais diferenciados foram observados quando o grupo triazeno é inserido na porfirina, fazendo com que estes novos compostos apresentem novas propriedades quanto, por exemplo, às fragmentações no estado gasoso, deslocamento batocrômico nos espectros eletrônicos de absorção, variação das intensidades relativas e nos valores dos rendimentos quânticos de fluorescência, deslocalização eletrônica nos orbitais de fronteira evidenciando as transições de transferência de carga do ânion triazenido para o anel porfirínico e variações nos processos redox dos compostos até então estudados
Title in English
Synthesis, spectroscopical and electrochemical properties of triazene-porphyrin
Keywords in English
Charge-transfer
Donor-aceptor systems
Heterocyclic compounds
Porphyrin synthesis
Porphyrins
Triazenes
Triazenes-porphyrins
Abstract in English
In this thesis we has been developed a new class of supramolecular porphyrins containing (4-nitrophenyl)triazene group connected in the meso-aryl-position of the porphyrin ring. Their structural and electronic properties were investigated by mass spectrometry, absorption and emission electronic spectroscopy, semi-empirical theoretical calculations, nuclear magnetic resonance of 1H and 13C-NMR, cyclic voltammetry and spectroelectrochemistry. Different structural and electronic effects were observed when the unit is inserted into the triazene to porphyrin, so that these presents new properties such as, for example, to fragmentation in the gaseous state, bathocrimic shift in the electronic absorption spectra, relative intensity variation and values the fluorescence quantum yields, electron delocalization in the frontier orbitals showing the charge-transfer transitions from the triazenide anion to the porphyrin ring and changes in redox processes of compounds previously studied.
 
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Publishing Date
2012-10-24
 
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