Indenofluorene-Extended Tetrathiafulvalene Scaffolds for Dye-Sensitized Solar Cells
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Indenofluorene-Extended Tetrathiafulvalene Scaffolds for Dye-Sensitized Solar Cells. / Mogensen, Josefine; Michaels, Hannes; Roy, Rajarshi; Brolos, Line; Kilde, Martin Drohse; Freitag, Marina; Nielsen, Mogens Brondsted.
I: European Journal of Organic Chemistry, Bind 2020, Nr. 38, 10.09.2020, s. 6127-6134.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Indenofluorene-Extended Tetrathiafulvalene Scaffolds for Dye-Sensitized Solar Cells
AU - Mogensen, Josefine
AU - Michaels, Hannes
AU - Roy, Rajarshi
AU - Brolos, Line
AU - Kilde, Martin Drohse
AU - Freitag, Marina
AU - Nielsen, Mogens Brondsted
PY - 2020/9/10
Y1 - 2020/9/10
N2 - Indenofluorene-extended tetrathiafulvalenes (IF-TTFs) comprise a class of pi-conjugated sensitizers that exhibit strong absorptions in the visible region and two reversible one-electron oxidations. Herein we present the synthesis and optical as well as redox properties of novel IF-TTF donor-acceptor scaffolds that were integrated in dye-sensitized solar cells (DSCs) via anchoring of a carboxylic acid end-group on the scaffolds to TiO2. Synthetically, the scaffolds were constructed by Sonogashira coupling reactions between an iodo-functionalized IF-TTF and an acceptor moeity containing a terminal alkyne. These very first IF-TTF based candidates for DSCs exhibited high performances, in particular a dye incorporating a benzothiadiazole acceptor moiety, showing a conversion efficiency of 6.4 %. This result signals that IF-TTF derivatives present a promising class of compounds for further structural modifications. Such modifications will benefit from the readiness of the iodo-funcitonalized IF-TTF building block to undergo Pd-catalyzed coupling reactions.
AB - Indenofluorene-extended tetrathiafulvalenes (IF-TTFs) comprise a class of pi-conjugated sensitizers that exhibit strong absorptions in the visible region and two reversible one-electron oxidations. Herein we present the synthesis and optical as well as redox properties of novel IF-TTF donor-acceptor scaffolds that were integrated in dye-sensitized solar cells (DSCs) via anchoring of a carboxylic acid end-group on the scaffolds to TiO2. Synthetically, the scaffolds were constructed by Sonogashira coupling reactions between an iodo-functionalized IF-TTF and an acceptor moeity containing a terminal alkyne. These very first IF-TTF based candidates for DSCs exhibited high performances, in particular a dye incorporating a benzothiadiazole acceptor moiety, showing a conversion efficiency of 6.4 %. This result signals that IF-TTF derivatives present a promising class of compounds for further structural modifications. Such modifications will benefit from the readiness of the iodo-funcitonalized IF-TTF building block to undergo Pd-catalyzed coupling reactions.
KW - Conjugation
KW - Cross-coupling
KW - Dyes
KW - Redox chemistry
KW - Sulfur heterocycles
KW - HIGHLY-EFFICIENT
KW - 2,1,3-BENZOTHIADIAZOLE
KW - PERFORMANCE
KW - DERIVATIVES
KW - PORPHYRIN
KW - ACCEPTOR
U2 - 10.1002/ejoc.202001058
DO - 10.1002/ejoc.202001058
M3 - Journal article
VL - 2020
SP - 6127
EP - 6134
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 38
ER -
ID: 248803681