13170-43-9Relevant articles and documents
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Whitmore,Sommer
, p. 481,483 (1946)
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Self-organisation through size-exclusion in soft materials
Mandle, Richard J.,Davis, Edward J.,Voll, Constantin-Christian A.,Lewis, Daniel J.,Cowling, Stephen J.,Goodby, John W.
supporting information, p. 2380 - 2388 (2015/04/14)
A number of materials derived from 4-undecyloxy-4′-cyanobiphenyl but with varying terminal groups were prepared in order to better understand how such a group influences the type, and local structure of mesophases formed. Whereas electron poor terminal groups (fluoroaromatics and halogen atoms) were found to destabilise the smectic A phase through unfavourable electrostatic interactions, bulky silane, siloxane and hydrocarbon groups can be incorporated into the structure of the phase with only minor reductions in clearing point. An increase in the layer spacing of the smectic Ad phase in materials with bulky groups suggests that microphase segregation is not the driving force, but rather exists as a consequence of steric crowding at the smectic layer interface. Electrooptic studies reveal that 'carbosilane' end groups, such as tetramethyldisilapropane, are significantly more electrochemical stable than their siloxane counterparts whilst retaining their desirable thermal properties.
Palladium-catalyzed kumada coupling reaction of bromoporphyrins with silylmethyl grignard reagents: Preparation of silylmethyl-substituted porphyrins as a multipurpose synthon for fabrication of porphyrin systems
Sugita, Noriaki,Hayashi, Satoshi,Hino, Fumio,Takanami, Toshikatsu
, p. 10488 - 10497 (2013/02/22)
We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbona-carbon single and double bonds.
