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Two‐Dimensional Nanostructures by the Assembly of n ‐Type Tetraazaanthracene‐Based Conjugated Molecules
Author(s) -
He Chunyang,
Wu Dongqing,
Zhang Fan,
Xue Minzhao,
Zhuang Xiaodong,
Qiu Feng,
Feng Xinliang
Publication year - 2013
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201300444
Subject(s) - alkyl , molecule , conjugated system , nanostructure , chemistry , self assembly , heteroatom , solvent , thiophene , crystallography , materials science , polymer , nanotechnology , organic chemistry
On the basis of our previous communication concerning a new family of thiophene‐armed tetraazaanthracene molecules, we present a further intensive investigation on this class of compounds substituted with different alkyl chains and their self‐assembled two‐dimensional (2D) nanostructures. These tetraazaanthracene molecules with different alkyl chains were prepared in good yields using the synthetic strategy we developed. In addition to the expected typical n ‐type character, one compound exhibited aggregation behavior upon electrochemical reduction. Moreover, all molecules in the neutral state showed a strong tendency to aggregate in a binary solvent, as confirmed by optical spectral measurements. To investigate such self‐assembly behavior, a phase‐transfer method with a dichloromethane/methanol (2:3) binary solvent system was used to prepare the nanostructures. By means of atomic force microscopy, transmission electron microscopy, and X‐ray diffraction, we found that the morphology of assembled 2D sheet‐like structures could be adjusted by varying the alkyl chain. The weak interactions arising from the heteroatoms (N and S) in the conjugated backbones play a key role in the formation and stabilization of layered structures.