Supramolecular Self-assembly of Discotic Liquid Crystalline LEGOs
Discotic liquid crystals with well-defined columnar self-assemblies are promising for technological applications in organic electronics such as organic solar cells and field-effect transistors. In this entry, we review the self-assembly behavior of discotic supermolecules comprised of various discotic and cubic building blocks, including porphyrin, phthalocyanine, triphenylene, and polyhedral oligomeric silsesquioxane (POSS). With the help of amide hydrogen bonding, triphenylenes and porphyrins stack into the ordered “lamello-columnar” phase. Without hydrogen bonding interaction, the π-π stacking interaction leads to a hexagonal columnar phase with mixed phthalocyanine and triphenylene columns. For a POSS molecule covalently attached to eight triphenylenes, the triphenylenes and the POSS core can form a super-column when the space length is short. Self-assembly of these supercolumns can lead to a hexagonal superlattice. From this study, the spacer length, molecular geometry/size, and intermolecular interactions play an important role in the self-assembly of the discotic liquid crystalline LEGOs.
KeywordsDiscotic liquid crystals Columnar self-assembly Hydrogen bonding Triphenylene Phthalocyanine Porphyrin Polyhedral oligomeric silsesquioxane (POSS)
This work was supported by the National Science Foundation CAREER Award (DMR-0348724), DuPont Young Professor Award, and 3M Nontenured Faculty Award.
- Benanti TL, Saejueng P, Venkataraman D (2007) Segregated assemblies in bridged electron-rich and electron-poor π-conjugated moieties. Chem Commun (7):692–694Google Scholar
- Charvet R, Yamamoto Y, Sasaki T, Kim J, Kato K, Takata M, Saeki A, Seki S, Aida T (2012) Segregated and alternately stacked donor/acceptor nanodomains in tubular morphology tailored with zinc porphyrin-C60 amphiphilic dyads: clear geometrical effects on photoconduction. J Am Chem Soc 134(5):2524–2527CrossRefGoogle Scholar
- Dossel LF, Kamm V, Howard IA, Laquai F, Pisula W, Feng XL, Li C, Takase M, Kudernac T, De Feyter S, Mullen K (2012) Synthesis and controlled self-assembly of covalently linked hexa-peri-hexabenzocoronene/perylene diimide dyads as models to study fundamental energy and electron transfer processes. J Am Chem Soc 134(13):5876–5886CrossRefGoogle Scholar
- Ichihara M, Suzuki A, Hatsusaka K, Ohta K (2007) Discotic liquid crystals of transition metal complexes 38: peripheral chain substituent position effect on columnar mesophase and stacking structures of novel phthalocyanine-based liquid crystals. J Porphyrins Phthalocyanines 11(7):503–512CrossRefGoogle Scholar
- Li WS, Yamamoto Y, Fukushima T, Saeki A, Seki S, Tagawa S, Masunaga H, Sasaki S, Takata M, Aida T (2008) Amphiphilic molecular design as a rational strategy for tailoring bicontinuous electron donor and acceptor arrays: photoconductive liquid crystalline oligothiophene-C60 dyads. J Am Chem Soc 130(28):8886–8887CrossRefGoogle Scholar
- Mahlstedt S, Janietz D, Stracke A, Wendorff JH (2000) First triphenylene based non-symmetric donor-acceptor triple mesogen possessing disc-like and rod-like characteristics. Chem Commun (1):15–16Google Scholar
- Zeng DL, Tahar-Djebbar I, Xiao YM, Kameche F, Kayunkid N, Brinkmann M, Guillon D, Heinrich B, Donnio B, Ivanov DA, Lacaze E, Kreher D, Mathevet F, Attias AJ (2014) Intertwined lamello-columnar coassemblies in liquid-crystalline side-chain π-conjugated polymers: toward a new class of nanostructured supramolecular organic semiconductors. Macromolecules 47(5):1715–1731CrossRefGoogle Scholar