Chiroptical molecular switch

Scheme 1 Potential applications of a chiral optical (chiroptical) molecular switch.

Feringa BL, van Delden RA, ter Wiel MKJ. Chiroptical molecular switch In Fering BL, Ed. Molecular Switches. Weinheim Wiley-VCH, 2001 123-163. 

The concepts learned from the examples in Fig. 3 have been used to develop more complex and efficient systems. The idea of trans-cis isomerization, for instance, has led to the construction of a molecule that may be converted between its states by the use of circularly polarized light (Fig. 4) [23]. The alkene 7 is forced to adopt a chiral conformation as a consequence of its steric requirements, allowing isomerization between the trans- and ds-states (7a and 7b) to be accomplished. The state of the system can be monitored easily by measuring the rotation of linearly polarized light. The construction of these chiroptical molecular switches is of great interest because of their ability to be both written to and read by non-interfering photonic means [24]. 

Chiroptical molecular switches (photochromic compounds among them dihetarylethenes, fulgides, and spiropyrans permitting undestructive read-out of information using change of optical rotation 00CRV1789. 

A stereospecific photochemical switching process provided a useful basis for chiroptical molecular switches and molecular memory elements (07CC1745). 

Feringa BL, van Delden RA, Koumura N, Geertsema EM. 2000. Chiroptical molecular switches. Chem Rev 100(5) 1789 1816. 

R.A. van Delden, T. Mecca, C. Rosini, B.L. Feringa, A chiroptical molecular switch with distinct chiral and photochromic entities and its application in optical switching of a cholesteric liquid crystal. Chem. Eur. J. 10, 61-70 (2004)... 

D. Pijper, M.G.M. Jongejan, A. Meetsma, B.L. Feringa, Light-controlled supramolecular helicity of a liquid crystalline phase using a helical polymer functionalized with a single chiroptical molecular switch. J. Am. Chem. Soc. 130, 4541 552 (2008)... 

R.A. van Delden, M.B. van Gelder, N.P.M. Huck, B.L. Feringa, Controlling the color of cholesteric liquid-crystalline films by photoirradiation of a chiroptical molecular switch used as dopant. Adv. Funct. Mater. 13, 319-324 (2003)... 

Leigh et al. also reported a chiroptical molecular switch (Figure 63) with a large amplitude displacement of a tetraamide macrocycle driven by light. The tetraamide macrocycle resides on the fumaramide unit of the dumbbell component initially. Upon photoisomerization of the... 

Figure 63 A photo-driven chiroptical molecular switch based on a peptide rotaxane.

In 1991, Feringa etal. synthesized a chiroptical molecular switch (Figure 86) based on pseudoenantiomeric forms, P and M (indicating the opposite heUcity, P denotes the right-handed heUcity and M stands for the left-handed... 

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