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Aggregation-Induced Emission Enhancement and Aggregation-Induced Circular Dichroism of chiral Pentaphenylpyrrole Derivatives and Their Helical Self-Assembly

Abstract

A pair of enantiomers (S)-PPPtriAm and (R)-PPPtriAm with three chrial substituents and their raceme rac-PPPtriAm derived from conjugated luminogens pentaphenylpyrrole were prepared by covalently attaching (R)-/(S)- or racemic 1-phenylethylamine to conjugated 1-biphenyl-2,3,4,5-tetraphenyl pyrrole. The compounds exhibit obviously aggregation-induced emission enhancement (AIEE) features, the chiral substituent have little effect on the photophysical properties. More importantly, the introduction of chiral substituents endows the chiral compounds (S)-PPPtriAm and (R)-PPPtriAm with distinct aggregation-induced circular dichroism (AICD) with mirror-image Cotton effects, and chiral-polarized luminescence (CPL) properties with emission dissymmetry factor (gem) in 0.5×10-3~5×10-3 for (S)-PPPtriAm and -1×10-3~-6×10-3 for (R)-PPPtriAm in DMSO-water mixture with water faction of 40%. The chiral compounds (S)-PPPtriAm and (R)-PPPtriAm can self-assemble into nanofibers, and the lank nanofibers orderly weave and align together to form regular arrangement aggregations. The raceme rac-PPPtriAm exhibits AIEE features without any AICD and CPL signals, and can self-assemble to form nanoparticle blocks. Herein, the enantiomers (S)-PPPtriAm and (R)-PPPtriAm, as AEE-active luminogens with multi-chiral substituent, are expected to have potential application in photoelectronic materials or to design optically active fluorophores for sensitive enantiomer recognition.

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Publication details

The article was received on 18 Feb 2017, accepted on 09 Jun 2017 and first published on 09 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ00583K
Citation: New J. Chem., 2017, Accepted Manuscript
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    Aggregation-Induced Emission Enhancement and Aggregation-Induced Circular Dichroism of chiral Pentaphenylpyrrole Derivatives and Their Helical Self-Assembly

    L. Zhang, K. Liang, L. Dong, P. Yang, Y. Li, X. Feng, J. Zhi, J. Shi, B. Tong and Y. Dong, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ00583K

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