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Impact of Linear Alkyl Length on the Assembly of Twisted Perylene Bisimides: From Molecular Arrangement to Nanostructures
Author(s) -
Guo Zongxia,
Wang Kun,
Yu Ping,
Wang Xiangnan,
Lan Shusha,
Sun Kai,
Yi Yuanping,
Li Zhibo
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700984
Subject(s) - stacking , alkyl , perylene , nanostructure , van der waals force , materials science , lamellar structure , solvent , molecule , fourier transform infrared spectroscopy , fluorescence , crystallography , imine , chemical engineering , nanotechnology , chemistry , organic chemistry , optics , physics , engineering , catalysis
The effect of the length of linear alkyl chains substituted at imine positions on the assembly of tetrachlorinated perylene bisimides ( 1 : PBI with −C 6 H 13 ; 2 : PBI with −C 12 H 25 ) has been investigated. Solvent‐induced assembly was performed in solutions of THF and methanol with varying volume ratios. Morphological (SEM, AFM, and TEM) and spectral (UV/Vis, fluorescence, FTIR, and XRD) methods were used to characterize the assembled nanostructures and the molecular arrangement in the aggregates. It was found that uniform structures could be obtained for both molecules in solutions with a high ratio of methanol. PBI 1 formed rigid nanosheets, whereas 2 assembled into longer nanostripes with a high ratio of length to width. On combining the morphological data with the spectral data, it was suggested that π–π stacking predominated in assemblies of 1 , and the synergetic effect of van der Waals interactions from the long alkyl chains and π–π stacking between neighboring building blocks facilitated the growth of the long‐range‐ordered nanostructures of 2 . By changing the linear chain length, the hierarchical assembly of PBIs modified on bay positions could be manipulated effectively.