Photochromic switching behaviour of donor-acceptor Stenhouse adducts in organic solvents.
نویسندگان
چکیده
We report photochromic donor-acceptor Stenhouse adducts (DASAs) capable of fully reversible photoisomerization with visible light in organic solvents including chloroform, acetonitrile and benzene. The rates of photoisomerization and thermal reversion can be tuned by altering the electronics of the donor adduct. X-Ray crystallography and photo-NMR experiments unambiguously establish molecular structures.
منابع مشابه
Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles
Donor–acceptor Stenhouse adducts (DASAs) have recently emerged as a new class of photoswitchable molecules. 2] These compounds feature a system of three conjugated C=C double bonds connecting an aliphatic amine “donor” and a 1,3-dicarbonyl “acceptor”, giving rise to an intense absorption in the visible (green) region. DASAs serve as an example of negative photochromic materials : exposing the t...
متن کاملDesign and synthesis of donor-acceptor Stenhouse adducts: a visible light photoswitch derived from furfural.
The development of an easily synthesized, modular, and tunable organic photoswitch that responds to visible light has been a long-standing pursuit. Herein we provide a detailed account of the design and synthesis of a new class of photochromes based on furfural, termed donor-acceptor Stenhouse adducts (DASAs). A wide variety of these derivatives are easily prepared from commercially available s...
متن کاملShedding Light on the Photoisomerization Pathway of Donor–Acceptor Stenhouse Adducts
Donor-acceptor Stenhouse adducts (DASAs) are negative photochromes that hold great promise for a variety of applications. Key to optimizing their switching properties is a detailed understanding of the photoswitching mechanism, which, as yet, is absent. Here we characterize the actinic step of DASA-photoswitching and its key intermediate, which was studied using a combination of ultrafast visib...
متن کاملControlled drug release to cancer cells from modular one-photon visible light-responsive micellar system.
We present a one-photon visible light-responsive micellar system for efficient, on-demand delivery of small molecules. Release is mediated by a novel class of photochromic material - donor-acceptor Stenhouse adducts (DASAs). We demonstrate controlled delivery of small molecules such as the chemotherapeutic agent (paclitaxel) to human breast cancer cells triggered by micellar switching with low ...
متن کاملA ‘‘reverse interrupter’’: the novel molecular design of a fluorescent photochromic DTE-based bipyridinew
Fluorescent switching systems containing photochromic molecules have attracted significant attention on account of their potential uses as optical memory media and photoswitchable devices. Most systems offering the photomodulation of luminescence involve a photochrome covalently linked to an organic or metal–organic fluorophore, wherein the luminescence is regulated by an intramolecular energy ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 52 93 شماره
صفحات -
تاریخ انتشار 2016