Influence of Side-Chain on Structural Order and Photophysical Properties in Thiophene Based Diketopyrrolopyrroles: A Systematic Study

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• 作者：Mallari A. Naik ; N. Venkatramaiah ; Catherine Kanimozhi ; Satish Patil
• 刊名：The Journal of Physical Chemistry C
• 出版年：2012
• 出版时间：December 20, 2012
• 年：2012
• 卷：116
• 期：50
• 页码：26128-26137
• 全文大小：548K
• 年卷期：v.116,no.50(December 20, 2012)
• ISSN：1932-7455

文摘

In this work, we have synthesized a series of TDPP derivatives with different alkyl groups such as n-hexyl (鈭扖₆H₁₃) 3a, 2-ethylhexyl (-(2-C₂H₅)C₆H₁₂) 3b, triethylene glycol mono methyl ether (-(CH₂CH₂O)_3cH₃, TEG) 3c, and octadodecyl (-(8-C₈H₁₇)C₁₂H₂₂) 3d. N,N dialkylation of thiophene-diketopyrrolopyrrole (TDPP, 1) strongly influences its solubility, solid state packing, and structural order. These materials allow us to explicitly study the influence of alkyl chain on solid state packing and photophysical properties. TDPP moiety containing two different alkyl groups 3e (TEG and 2-ethylhexyl) and 3f (TEG and n-hexyl) were synthesized for the first time. The absorption spectra of all derivatives exhibited a red shift in solid state when compared to their solution spectra. The type of alkyl chains leads to change in the optical band gaps in solid state. The fluorescence study reveals that TDPP derivatives have strong 蟺鈥撓€ interaction in the solid state and the extent of bathochromic shift is due to combination of intramolecular interaction and formation of aggregates in solid state. This behavior strongly depends on the nature of alkyl chain. The presence of strong C鈥揌路路路O inter chain interactions and CH鈭捪€ interactions in solid state exhibits strong influence on the photophysical properties of TDPP chromophore.