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Título: | Tryptanthrin from indigo: Synthesis, excited state deactivation routes and efficient singlet oxygen sensitization | Autor: | Pinheiro, Daniela Piñeiro, Marta Pina, João Brandão, Pedro Galvão, Adelino M. Melo, J. Sérgio Seixas de |
Palavras-chave: | Indigo; Tryptanthrin; Fluorescence; Singlet oxygen sensitization; TDDFT | Data: | Abr-2020 | Editora: | Elsevier | Projeto: | info:eu-repo/grantAgreement/RCUK/Innovate UK/103252/GB/HYLIGHT – HYbrid LIquefied petroleum Gas tanker witH magspliT info:eu-repo/grantAgreement/UID/QUI/00313/2019 info:eu-repo/grantAgreement/POCI-01-0145-FEDER-016387/SunStorage - Harvesting and storage of solar energy info:eu-repo/grantAgreement/UID/QUI/00100/2019 info:eu-repo/grantAgreement/SFRH/BD/74351/2010 info:eu-repo/grantAgreement/PD/BD/128490/2017 |
Título da revista, periódico, livro ou evento: | Dyes and Pigments | Volume: | 175 | Número: | 108125 | Resumo: | The microwave-assisted synthesis of tryptanthrin from indigo in mild oxidation conditions, and a comprehensive study of the excited state properties of this compound in a variety of solvents with different polarity and viscosity values at room and low temperatures are reported. In contrast with indigo, emission of the triplet state of tryptanthrin is observed with a very efficient singlet oxygen sensitization quantum yield, indicating that the triplet state is efficiently populated. From time-resolved fluorescence and femtosecond transient absorption data, further supported with time-dependent density functional theory (TDDFT) calculations, two species, with S1 states with locally excited (LE) of π,π* nature and a charge transfer (CT) of n,π* characteristics, originated from an initially populated Frank-Condon S2 state (π,π*), are observed. The two electronically independent species are energetically nearly degenerate and inter-conversion is predicted (and rate constants determined) to occur between LE (S1) and CT (S1) species. Due to the low value of the fluorescence quantum yield (~10−3) and high triplet state yield (ϕT≥ϕΔ), the high stability of this compound is associated to the high efficiency of the radiationless deactivation processes which involve the formation of the CT state which efficiently converts, through S1 ~~> Tn intersystem crossing, to the T1 triplet state. | URI: | https://hdl.handle.net/10316/91076 | ISSN: | 01437208 | DOI: | 10.1016/j.dyepig.2019.108125 | Direitos: | embargoedAccess |
Aparece nas coleções: | I&D CQC - Artigos em Revistas Internacionais |
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DP_2020.pdf | 1.07 MB | Adobe PDF | Ver/Abrir |
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