Improved photovoltaic performance of D–A–D-type small molecules with isoindigo and pyrene units by inserting different π-conjugated bridge

Recent advances in the application of isoindigo derivatives in materials chemistry

“…At the same time, pyrene-1-ylboronic acid and 6,6'-dibromoisoindigo were used to introduce a pyrene fragment directly into the isoindigo nucleus, and to obtain a thiophene analogue, pyrenyl-substituted 2-bromothiophene and 6,6'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindigo were used (Scheme 6). Thus, a photovoltaic cell based on thiophene derivative 7 mixed with PC 71 BM showed an efficiency of 1.88% [19], but if the pyrenyl substituent is bonded directly to the isoindigo core, the efficiency of such an OSC turns out to be significantly lower (0.10%) [20]. One of the highest efficiency values (4.7%) among low-molecular-weight isoindigo derivatives was shown by a two-component OSC based on isoindigo 9a, containing an alkoxylated p-phenylene fragment and PC 71 BM in a ratio of 1:0.7 (w/w), a thin film of which was obtained from chloroform with 0.5 vol % N-methylpyrrolidone (Scheme 7).…”

“…At the same time, pyrene-1-ylboronic acid and 6,6'-dibromoisoindigo were used to introduce a pyrene fragment directly into the isoindigo nucleus, and to obtain a thiophene analogue, pyrenyl-substituted 2-bromothiophene and 6,6'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindigo were used ( Scheme 6 ). Thus, a photovoltaic cell based on thiophene derivative 7 mixed with PC 71 BM showed an efficiency of 1.88% [ 19 ], but if the pyrenyl substituent is bonded directly to the isoindigo core, the efficiency of such an OSC turns out to be significantly lower (0.10%) [ 20 ].…”

Base-Promoted (5 + 2) Annulation between 2(Alkynylaryl)acetonitriles and Arylalkynes for the Synthesis of Benzocycloheptene Derivatives

“…(d) Synthetic Procedure for 6 [3] A mixture of 7-(4-bromophenyl)-6-phenyl-5H-benzo [7]annulene-9-carbonitrile (3af, 0.1 mmol, 39.7 mg), allyltributylstannane (0.3 mmol, 95.4 mg), Pd(PPh3)4 (10 mol %, 11.6 mg) and 1.5 mL of toluene was added to a resealable Schlenk tube under nitrogen atmosphere. The mixture was stirred at 100 ℃ for 16 h. Then the resulting mixture was extracted with ethyl acetate.…”