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A New Synthetic Route to Cycloheptatrienylidene Fluorophores
Author(s) -
David Navindra,
Hyatt Ivan Fabe Dempsey
Publication year - 2019
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.2019.33.1_supplement.635.4
Subject(s) - stacking , chemistry , fluorophore , fluorescence , hypervalent molecule , combinatorial chemistry , luminescence , quenching (fluorescence) , aggregation induced emission , molecule , nanotechnology , reagent , organic chemistry , materials science , optoelectronics , physics , quantum mechanics
Luminescent molecules can lose their fluorescent properties through aggregation caused quenching (ACQ). ACQ is caused when these molecules, in high concentration, undergo π‐π stacking. Previous methods have been developed that utilize Aggregate Induced Emission (AIE) mechanisms to avoid the π‐π stacking. Analyzing how to turn on this AIE mechanism through aggregation with a metal can stop this stacking phenomena and allow the molecule to exhibit fluorescence in a concentrated solution. One known fluorophore that exhibits AIE properties are cycloheptatrienylidenes (CHT). The project described herein uses hypervalent iodine in a new methodology to synthesize CHTs. A faster and cheaper way to synthesize asymmetric CHTs is being investigated for the generation of AIE materials. Currently, methodologies of producing symmetrical cycloheptatrienylidene fluorophores are expensive, time consuming, and involve multiple steps. Ongoing reactions involve synthesizing the CHT using a modified Catellani reaction. The Catellani reaction has eliminated a number of steps in creating the precursor to the CHT. Production of AIE fluorophores that will “turn‐on” fluorescence after coming into contact with metals could be used to activate endogenous metals in the body which could help to target malignancies such as cancer. This abstract is from the Experimental Biology 2019 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .