2007
DOI: 10.1002/chem.200700130
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Chiral Supramolecular Assemblies of a Squaraine Dye in Solution and Thin Films: Concentration‐, Temperature‐, and Solvent‐Induced Chirality Inversion

Abstract: We prepared novel cholesterol-appended squaraine dye 1 and model squaraine dye 2 and investigated their aggregation behavior in solution and thin films using photophysical, chiroptical, and microscopic techniques. Investigations on the dependence of aggregation on solvent composition (good/poor, CHCl3/CH3CN) demonstrated that squaraine dye 1 forms two novel H-type chiral supramolecular assemblies with opposite chirality at different good/poor solvent compositions. Model compound 2 formed J-type achiral assembl… Show more

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Cited by 81 publications
(59 citation statements)
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“…Both isodesmic and cooperative models have been used extensively to describe the SP of multiple compounds into a single, thermodynamically controlled aggregate . However, self‐assembled systems, particularly those governed by a cooperative mechanism, often exist as more than one single structure, which suggests that kinetic contributions should also be considered when analyzing self‐assembly processes . Thus, the parameter time also contributes drastically to the final outcome of the corresponding SP.…”
Section: General Aspects Of Supramolecular Polymerizationmentioning
confidence: 99%
“…Both isodesmic and cooperative models have been used extensively to describe the SP of multiple compounds into a single, thermodynamically controlled aggregate . However, self‐assembled systems, particularly those governed by a cooperative mechanism, often exist as more than one single structure, which suggests that kinetic contributions should also be considered when analyzing self‐assembly processes . Thus, the parameter time also contributes drastically to the final outcome of the corresponding SP.…”
Section: General Aspects Of Supramolecular Polymerizationmentioning
confidence: 99%
“…[15][16][17][18][19] Kinetic control was also observed in the case of self-assembly based on strong dipolar interactions of merocyanine dyes [20][21][22][23] (enabling unique supramolecular stereomutation [20] ) and squarine dyes. [24] Kinetically controlled processes in host-guest systems have been also reported. [25][26][27][28] Kinetically controlled self-organization of relatively small molecular amphiphiles in water has been recently shown to control self-replication in dynamic combinatorial libraries.…”
Section: Introductionmentioning
confidence: 96%
“…560 cm −1 ). The appearance of a hypsochromic band points towards H‐type aggregation of SQ6 , as has been observed for other squaraine dyes ,,. On the other hand, the small bandwidth of the H‐type band suggests well‐ordered aggregates.…”
Section: Resultsmentioning
confidence: 99%
“…Given that solvation effects were not considered in our model calculations but may interfere with the association of two squaraines in SQ6‐1 , the gas‐phase relative energies of the two species are only indicative of stabilities in solution but not definitive. In fact, for squaraine systems, the strong solvent‐dependence of structure formation has been reported in previous publications that report reduced aggregation in CHCl 3 . To account for this solvation effect in the calculation of optical properties, as a rough approximation, we carried out additional optimizations of the monomers without dispersion correction; these gave structures with the squaraine units almost uniformly distributed around the centred benzene core as one would expect for solvation with a good solvent [see Figure (b)].…”
Section: Resultsmentioning
confidence: 99%