Designed molecular propellers based on tetraarylterephthalamide and their chiroptical properties induced by biased helicity through transmission of point chirality.
نویسندگان
چکیده
The syn-atropisomers of the title bis(tertiary amide)s were designed as six-bladed molecular propellers based on the "directing effects" of amide dipoles; the helicity of the propeller is biased to prefer one handedness upon the attachment of point chirality to the amide nitrogens to attain stronger circular-dichroism activity than for the non-propeller-shaped anti-isomers.
منابع مشابه
Chiroptical molecular propellers based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality.
We designed hexakis(phenylethynyl)benzene derivatives with a tertiary amide group on each blade to achieve a helically biased propeller arrangement through the complexation-induced intramolecular transmission of point chirality. A hydrogen-bonding ditopic guest was captured at two amide groups, and thus could pair two neighboring blades to form a supramolecular cyclic structure, in which an aux...
متن کاملA C(3)-symmetric chiroptical molecular propeller based on hexakis(phenylethynyl)benzene with a threefold terephthalamide: stereospecific propeller generation through the cooperative transmission of point chiralities on the host and guest upon complexation.
Propeller-shaped dynamic helicity was generated in a hexakis(phenylethynyl)benzene framework that preferred a particular sense to afford a strong CD signal, which was realized by the cooperative transmission of point chiralities upon complexation with a chiral guest through a threefold binding site presented by a syn-formed terephthalamide.
متن کاملChiroptical Properties and Conformation of 4,5-Saturated Derivatives of 5-Aryl-l,4-benzodiazepin-2-ones
CD spectra of a series of 5-aryl-7-chloro-l,3,4,5-tetrahydro2H-l,4-benzodiazepin-2-one derivatives having different substituents at positions 1, 3, 4, and 5 were studied. The absolute eonfiguration at C-5 of two homochiral analogues, 1 and 2, having enantiomorphous ring conformations was determined on the basis of chiroptical correlations and theoretical calculations. The latter have shown that...
متن کاملChiral imides as potential chiroptical switches: synthesis and optical properties
A series of chiral aromatic imides and diimides were synthesized and their electrochemical, absorption, fluorescent, and chiroptical properties were examined for their potential application as molecular chiroptical switches. These compounds exhibit strong UV–vis absorptions, and can be electrochemically reduced to radical anions that absorb in the near infrared (NIR) region. Further reduction t...
متن کاملComplexation-induced inversion of helicity by an organic guest in a dynamic molecular propeller based on a tristerephthalamide host with a two-layer structure.
A tristerephthalamide host exhibited two helical geometries with (M)- and (P)-helicity, respectively, in terms of the twisting direction of a two-layer structure, and the helical preference switched upon complexation with a ditopic guest. In both uncomplexed and complexed states, the intramolecular transmission of chirality was responsible for the control of helicity.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 40 شماره
صفحات -
تاریخ انتشار 2008