2014
DOI: 10.1002/chem.201402093
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Elucidating the Structure–Property Relationships of Donor–π‐Acceptor Dyes for Dye‐Sensitized Solar Cells (DSSCs) through Rapid Library Synthesis by a One‐Pot Procedure

Abstract: The creation of organic dyes with excellent high power conversion efficiency (PCE) is important for the further improvement of dye-sensitized solar cells. We wish to describe the rapid synthesis of a 112-membered donor-π-acceptor dye library by a one-pot procedure, evaluation of PCEs, and elucidation of structure-property relationships. No obvious correlations between ε, and the η were observed, whereas the HOMO and LUMO levels of the dyes were critical for η. The dyes with a more positive E(HOMO), and with an… Show more

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Cited by 50 publications
(31 citation statements)
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“…We planned to couple donor block I with the aromatic scaffold of II because the C−Br bond of the first coupling product would be less reactive relative to the corresponding C−Br bond of the aromatic scaffold II . Therefore, an undesirable overreaction that afforded a D‐A′‐D compound would be suppressed (Figure ) . A one‐pot Suzuki–Miyaura (SM) coupling with III would afford the desired coupling product IV .…”
Section: Resultsmentioning
confidence: 99%
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“…We planned to couple donor block I with the aromatic scaffold of II because the C−Br bond of the first coupling product would be less reactive relative to the corresponding C−Br bond of the aromatic scaffold II . Therefore, an undesirable overreaction that afforded a D‐A′‐D compound would be suppressed (Figure ) . A one‐pot Suzuki–Miyaura (SM) coupling with III would afford the desired coupling product IV .…”
Section: Resultsmentioning
confidence: 99%
“…The microwave‐irradiation conditions shortened the reaction time from 8 to 3 hours, and slightly improved the yield of the desired product (Table , entry 2). The SM coupling of A′ with D2 and D4 , which contained our originally developed fused‐ring structure, was examined under microwave‐irradiation conditions (Table , entries 3 and 4). The use of D2 afforded better results.…”
Section: Resultsmentioning
confidence: 99%
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“…4,7-dibromo- [1,2,5]thiadiazolo [3,4-c]pyridine (1) [11], (4-(diphenylamino)phenyl)boronic acid (3) [12], (9-hexyl-9H-carbazol-3-yl)boronic acid (4) [13], tert-butyl 2-cyano-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate (5) [14] and tert-butyl 2-cyano-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)acrylate (6) [14] were prepared according to the published methods and characterized by NMR spectra. The synthetic routes for these building blocks are shown in Scheme 2.…”
Section: Materials and Reagentsmentioning
confidence: 99%