Two-dimensional self-assembly of single-, poly- and co-crystals at the liquid/solid interface

被引:10
作者
Liu, Pei [1 ]
Miao, Xinrui [1 ]
Li, Zhuomin [1 ]
Zha, Bao [1 ]
Deng, Wenli [1 ]
机构
[1] S China Univ Technol, Coll Mat Sci & Engn, Guangzhou 510640, Guangdong, Peoples R China
来源
CRYSTENGCOMM | 2014年 / 16卷 / 41期
基金
中国国家自然科学基金;
关键词
CONJUGATED OLIGOMERS; GRAPHITE; FLUORENONE; POLYFLUORENE; ARCHITECTURES; TRANSITIONS; MOLECULES; THIOPHENE; ALIGNMENT; DYNAMICS;
D O I
10.1039/c4ce01183j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Studying two-dimensional (2D) and three-dimensional (3D) crystallization in tandem is a powerful way to acquire a deep understanding of molecular self-assembly. X-ray crystallography results indicate that N-[6-(fluoren-9-ylideneamino)hexyl]fluoren-9-imine (C1), N-[12-(fluoren-9-ylideneamino) dodecyl]fluoren-9-imine (C2), and co-crystal of naphthalene-1,5-diamine and 9-fluorenone (C3) are single-, poly- and co-crystals, respectively. Furthermore, the self-assembled structures of these three kinds of crystals (C1, C2 and C3) at the 1-phenyloctane/HOPG interface are investigated using scanning tunneling microscopy under ambient conditions. The C1 molecule, with a short chain, is lying flat on the substrate with a close packing phase, which is the same in its 3D crystal structure. The C2 molecule, bearing a longer chain, forms two types of linear structures, which are stable enough to endure continuous tip scanning. In Type I, the C2 molecules lie flat on the substrate to form a linear zigzag pattern, while in Type II one of the fluorene cores in each C2 molecule adopts an edge-on arrangement and interlocks with the adjacent fluorene core in one lamella. In the co-crystal C3, naphthalene-1,5-diamine and 9-fluorenone arrange perpendicular to the HOPG surface in a herringbone pattern via hydrogen bonds and pi-pi interactions. The lying or standing orientation of the three kinds of crystals show that the functional groups tethered to the middle spacer can modulate the motifs of self-assembly in the 2D and 3D crystallization. Furthermore, it also highlights that physical adsorption on the HOPG surface is not only controlled by the adsorbate-substrate interactions but also by the size and shape of the adsorbates.
引用
收藏
页码:9690 / 9696
页数:7
相关论文
共 38 条
[1]   Bis-amino Acid Derivatives of 1,1′-Ferrocenedicarboxylic Acid: Structural, Electrochemical, and Metal Ion Binding Studies [J].
Adhikari, Bimalendu ;
Lough, Alan J. ;
Barker, Bryan ;
Shah, Afzal ;
Xiang, Cuili ;
Kraatz, Heinz-Bernhard .
ORGANOMETALLICS, 2014, 33 (18) :4873-4887
[2]   Two-dimensional self-assembly and complementary base-pairing between amphiphile nucleotides on graphite [J].
Bestel, Isabelle ;
Campins, Nathalie ;
Marchenko, Alexandr ;
Fichou, Denis ;
Grinstaff, Mark W. ;
Barthelemy, Philippe .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2008, 323 (02) :435-440
[3]   Self-assembly of polypeptide-based copolymers into diverse aggregates [J].
Cai, Chunhua ;
Wang, Liquan ;
Lin, Jiaping .
CHEMICAL COMMUNICATIONS, 2011, 47 (40) :11189-11203
[4]  
Claessens CG, 1997, J PHYS ORG CHEM, V10, P254, DOI 10.1002/(SICI)1099-1395(199705)10:5<254::AID-POC875>3.0.CO
[5]  
2-3
[6]   Electrical field-induced alignment of nonpolar hexabenzocoronene molecules into columnar structures on highly oriented pyrolitic graphite investigated by STM and SFM [J].
Cristadoro, Anna ;
Ai, Min ;
Raeder, Hans Joachim ;
Rabe, Juergen P. ;
Muellen, Klaus .
JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (14) :5563-5566
[7]   Field-force alignment of disc-type π systems [J].
Cristadoro, Anna ;
Lieser, Guenter ;
Raeder, Hans Joachim ;
Muellen, Klaus .
CHEMPHYSCHEM, 2007, 8 (04) :586-591
[8]   Co-crystal structure and optical properties of 9-fluorenone and naphthalene-1, 5-diamine [J].
Ding, K. K. ;
Pan, C. P. .
CRYSTALLOGRAPHY REPORTS, 2013, 58 (04) :604-607
[9]   Cooperative Supramolecular Polymerization: Comparison of Different Models Applied on the Self-Assembly of Bis(merocyanine) Dyes [J].
Fernandez, Gustavo ;
Stolte, Matthias ;
Stepanenko, Vladimir ;
Wuerthner, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (01) :206-217
[10]  
Gibb C.L. D., 2001, J. Supramol. Chem, V1, P39