Chiral memory via chiral amplification and selective depolymerization of porphyrin aggregates

Journal of the American Chemical Society

Volumn 132, Issue 47, 2010, Pages 16753-16755

  Helmich, Floris ^a   Lee, Cameron C ^a   Schenning, Albertus P H J ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL LIGATION; CHIRAL AMPLIFICATION; CHIRAL-MEMORY EFFECT; HELICITIES; LEWIS BASE; NEW APPROACHES; SUPRAMOLECULAR LEVEL;

AMPLIFICATION; STEREOCHEMISTRY; ZINC;

PORPHYRINS;

COPPER DERIVATIVE; LEWIS BASE; PORPHYRIN DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHIRALITY; CONFORMATION; COOLING; DEPOLYMERIZATION; EXTRACTION; HEATING; TEMPERATURE;

EID: 78649504614     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1077602     Document Type: Article

References (23)

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13. Chiral and achiral metal porphyrins were synthesized from commercially available meso -tetrakis(4-carboxyphenyl)porphyrin and a chiral/achiral trialkoxyaniline wedge. After amidation and metal insertion, the porphyrins were purified by column chromatography and recycling size-exclusion chromatography and fully characterized (12)
14. 3 (0.5 vol %) did not affect the aggregation. We refrained from "traditional" dissolution in MCH with subsequent heating/cooling (as shown earlier for S-Zn) (9) because A-Zn forms a different aggregate type upon cooling. (12)
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20. -7 M and a 100000-fold excess of QND, hydrogen bonding was not particularly favored; complexed monomeric species (sharp Soret band at 431 nm) rather than complexed dimers were formed. (9) Moreover, no changes in the UV-vis spectra were observed when QND was added to A-Cu homoaggregates (12)
21. Extraction was performed by stirring for 24 h in the absence of light.
22. On the basis of the g values from Figure 1 C (Figure S7b), (12) the reduction of the CD intensity is estimated to be >75% when 0.5% S-Zn remains co-aggregated.
23. The temperature-induced switching of the chiral memory was very sensitive to small differences in the experimental conditions (e.g., the heating and cooling rates). Unlike at RT, QND affected the H-type aggregation of A-Cu at higher temperatures (Figure S9b) (12)