Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/93142
Title: Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives
Authors: Pinheiro, Daniela 
Pineiro, Marta 
Galvão, Adelino M.
Melo, J. Sérgio Seixas de 
Issue Date: 2021
Project: 02/SAICT/2017 
PTDC/QUI-QFI/31625/2017 
info:eu-repo/grantAgreement/POCI-01-0145-FEDER-016387/SunStorage - Harvesting and storage of solar energy 
UIDB/00313/2020 
UIDP/00313/2020 
UID/QUI/00100/2019 
SFRH/BD/74351/2010SFRH/BD/74351/2010 
Serial title, monograph or event: Chemical Science
Volume: 12
Issue: 1
Abstract: Using green chemistry procedures the synthesis of N-alkyl (NCnInd) and N,N′-dialkyl (N,N′CnInd) indigo derivatives, with n = 1–3, 6, 8, 12 and 18, was undertaken, leading to compounds with blueish to greenish colors in solution. The effect of the alkyl chain length on the spectral (including color) and photophysical properties of the compounds was explored. This was done with solvents of different viscosities and polarities (dielectric constants). From time-resolved fluorescence and femtosecond-transient absorption (fs-TA) for the NCnInd derivatives with n = 1 and 2, the decays are, in methylcyclohexane (MCH) and n-dodecane, single-exponential, while in 2-methyltetrahydrofuran (2MeTHF) they are bi-exponential. The excited state proton transfer (ESPT) is ultrafast (<1 ps) for NC1,2Ind in MCH and n-dodecane, supported by time-dependent density functional theory (TDDFT) calculations, thus showing that both the chain length and solvent influence the ESPT process. For N,N′CnInd, from time-resolved experiments, and with the exception of the shortest member of the series, N,N′C1Ind, two conformers are found to be present in the excited state.
URI: http://hdl.handle.net/10316/93142
ISSN: 2041-6520
2041-6539
DOI: 10.1039/D0SC04958A
Rights: openAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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