Journal
DYES AND PIGMENTS
Volume 213, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2023.111136
Keywords
Quinoidal organic semiconductors; Perovskite solar cells; Conjugated polymers; Hole transport material; Indophenine dyes
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A new variant of the indophenine reaction was used to synthesize a series of quinoidal molecules. The previously reported method had low yield and selectivity, with the formation of by-products. A modified protocol using tertiary alcohol as a starting material was proposed to increase yield and avoid complex purification issues. The influence of the pi-bridge conjugation length on the electronic structure of the quinoidal compounds was investigated.
A series of quinoidal molecules were synthesized via a new variant of the indophenine reaction. The previously reported synthetic route of indophenine dyes involves a one pot procedure starting with isatin and an appropriate 5-membered aromatic heterocycle in the presence of catalytic amount of sulfuric acid. However, the reaction conditions lead to a low yield and a poor selectivity with the formation of several by-products. Herein, we propose a modification of the standard reaction to increase the yield, using tertiary alcohol as a starting material instead of isatin. This modified protocol is highly selective and allows for a very clean reaction, i.e. high yields, isomer-free synthesis and avoids any complex purification issues. Further, this protocol allows access to qui-noidal compounds with variable termini and pi-conjugated core. The influence of the conjugation length of the pi-bridge on the quinoidal electronic structure is investigated by spectroscopic and electrochemical measure-ments. Meanwhile, the charge carrier mobilities of selected compounds were determined by the space-charge -limited-current method. Their utility as a hole transport material for the perovskite solar cells is demonstrated.
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