1380497-22-2Relevant articles and documents
Improved crystallinity of the asymmetrical diketopyrrolopyrrole derivatives by the adamantane substitution
Cigánek, Martin,Heinrichová, Patricie,Kovalenko, Alexander,Ku?erík, Ji?í,Vala, Martin,Weiter, Martin,Kraj?ovi?, Jozef
, (2020)
Alkylation of diketopyrrolopyrroles (DPPs) is a powerful tool for increasing the solubility and processability of these pigments. Moreover, alkylation contributes to solid state packing and structural ordering of DPPs. In this study, the influence of the alkylation and solubilization side group engineering to DPPs on the thermal and optical properties was systematically investigated. Two series (each containing 3 derivatives: N,N'-, N,O′- and O,O′-substituted examples) of alkylated DPPs by 2-ethylhexyl and ethyladamantyl substituents were synthesized. Separation of all formed DPP derivatives was accomplished in order to perform an in-depth study of their physicochemical properties. DSC measurements revealed that the O-substitution caused a decrease in the thermal stability of DPP derivatives. On the contrary, an ethyladamantyl side chain, as a rigid alicyclic substituent, contributed very effectively to the increase of the melting point and thermal stability. The new results provide insights into the development of DPP-alkylated regioisomers and their thermal and optical properties.
Family of diazapentalene chromophores and narrow-band-gap polymers: Synthesis, halochromism, halofluorism, and visible-near infrared photodetectivity
Qian, Gang,Qi, Ji,Davey, James A.,Wright, James S.,Wang, Zhi Yuan
experimental part, p. 2364 - 2372 (2012/08/29)
A family of pyrrolo[3,4-c]pyrrol-1(2H)-one (PPO) and 2,5-diazapentalene (DAP) chromophores and DAP-containing polymers were synthesized, and their optical and electrochemical properties were studied. PPO and DAP chromophores are readily obtained by chemical transformation of the lactam unit in diketopyrrolopyrrole (DPP) dyes and can be used as versatile building blocks for construction of a variety of conjugated low-band-gap compounds and polymers. In comparison with the DPP chromophores, PPO and DAP chromophores have narrower energy gaps and low-lying HOMO levels in the order DPP > PPO > DAP. Interestingly, the PPO and DAP chromophores exhibit unique visible and near-infrared halochromic and halofluoric properties. The emission spectrum of DAP-containing polymer 6d covers the telecommunication window including the wavelength of 1310 nm. The photodetector with a device configuration of ITO/PEDOT:PSS (35 nm)/active layer (100 nm)/Al (100 nm) was fabricated using a blend of polymer 6d and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) in a weight ratio of 1:3 as the active layer and exhibited photocurrent spectral response from 400 to 1000 nm and the detectivity in an order of 1011 Jones at 800 nm.