Monitoring the dependence of the photovoltaic properties of dye-sensitized solar cells from the structure of D–A–π–A-type sensitizers with a 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole donor building block

Abstract

The potential of dye-sensitized solar cells (DSSCs) based on synthesized D-A-π-A type dyes with the 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole building block as a donor fragment was explored. The influence of the structure of...

5-(9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde

“…To synthesize the target 5-(9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde 2, we studied the direct C-H activation reactions between 6-bromo-9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole 1 (R = Br) [15] and thiophene-2-carbaldehyde (X = H) under the conditions previously described in the literature for similar transformations (Scheme 1) [16]. However, under the conditions studied, the reaction did not occur, and the starting compounds were recovered in almost quantitative yield (Table 1, entries 1-2).…”

“…However, under the conditions studied, the reaction did not occur, and the starting compounds were recovered in almost quantitative yield (Table 1, entries 1-2). The Suzuki reaction of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole 1 (R = Bpin 2 ) [15] with 5-bromothiophene-2-carbaldehyde (X = Br) resulted in compound 2 in moderate yield (Table 1, entry 3).…”

“…However, under the conditions studied, the reaction did not occur, and the starting compounds were recovered in almost quantitative yield (Table 1, entries 1-2). The Suzuki reaction of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole 1 [15] with 5bromothiophene-2-carbaldehyde (X = Br) resulted in compound 2 in moderate yield (Table 1, entry 3). The structure of 5-(9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6yl)thiophene-2-carbaldehyde 2 was confirmed by means high-resolution mass spectrometry, 1 H NMR, 13 C NMR, and IR spectroscopy.…”

“…6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole 1 (R = Bpin 2 ) was prepared according to the published method [15]. The solvents and reagents were purchased from commercial sources and used as received.…”

“…In this case, the donor (D) and acceptor (A) parts are connected to each other through a π bridge, designed to expand the conjugation chain and increase the distance traveled by the electron during excitation [11]. Typically, in the synthesis of D-π-A dyes, the last step is the well-known Knoevenagel reaction of D-π-aldehyde with cyanoacrylic acid [12,13], and Suzuki cross-couplings are most often employed for the preparation of a D-π-aldehydetype molecule [14,15]. Therefore, aldehyde synthesis is a key step in the preparation of the sensitizer.…”