Design and synthesis of benzothiadiazole-based molecular systems: self-assembly, optical and electronic properties
Por:
Miranda-Olvera, Montserrat, Arcos-Ramos, Rafael, Maldonado-Dominguez, Mauricio, Salmon, Lionel, Molnar, Gabor, Bousseksou, Azzedine, del Pilar Carreon-Castro, Maria
Publicada:
14 mar 2022
Resumen:
A set of small benzothiadiazole (BTD)-based derivatives with a D-A-D
architecture were synthesized and characterized as building blocks of
organic semiconducting materials by applying an experimental-theoretical
approach. The four derivatives tend to self-assemble into highly ordered
crystalline solids, with varying degrees of responsiveness to mechanical
and thermal stimuli. The featured derivatives exhibit absorption maxima
in solution and molar extinction coefficient values related to pi-pi*
electronic transitions with minor solvatochromic responses, displaying
broad fluorescence profiles with large Stokes shifts and high
fluorescence quantum yields. In the solid-state, the BTD derivatives
display absorption maxima in the visible range and intense fluorescence
emission of the n-butoxy and fluorene derivatives. The stability of the
one-electron reduced and oxidized forms of all compounds was assessed by
means of cyclic voltammetry, which complemented by DFT calculations
allowed the identification of one BTD derivative (BuO-BTD) as a strong
candidate for use as an electron transport layer in organoelectronic
devices.
Filiaciones:
Miranda-Olvera, Montserrat:
Univ Nacl Autonoma Mexico, Inst Ciencias Nucl, Dept Quim Radiac & Radioquim, Ciudad De Mexico 04510, Mexico
Lab Chim Coordinat, CNRS UPR 8241, 205 Route Narbonne, F-31077 Toulouse, France
Arcos-Ramos, Rafael:
Univ Nacl Autonoma Mexico, Inst Ciencias Nucl, Dept Quim Radiac & Radioquim, Ciudad De Mexico 04510, Mexico
Maldonado-Dominguez, Mauricio:
Czech Acad Sci, J Heyrovsky Inst Phys Chem, Dolejskova 2155-3, Prague 182238, Czech Republic
Salmon, Lionel:
Lab Chim Coordinat, CNRS UPR 8241, 205 Route Narbonne, F-31077 Toulouse, France
Molnar, Gabor:
Lab Chim Coordinat, CNRS UPR 8241, 205 Route Narbonne, F-31077 Toulouse, France
Bousseksou, Azzedine:
Lab Chim Coordinat, CNRS UPR 8241, 205 Route Narbonne, F-31077 Toulouse, France
del Pilar Carreon-Castro, Maria:
Univ Nacl Autonoma Mexico, Inst Ciencias Nucl, Dept Quim Radiac & Radioquim, Ciudad De Mexico 04510, Mexico
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