A series of electron‐rich π‐extended diindolotriazatruxene‐based compounds DIT, 4Py‐DIT (bearing pyrene units) and 4PyF‐DIT (bearing fluorene units) have been explored and investigated as fluorescence chemosensors. Quantitative analysis through fluorescence titrations showed that the resulting DIT molecules exhibited highly selective response to electron‐deficient nitroaromatic explosives. The calculated Stern‐Volmer quenching constants (>4.0×103 M−1) revealed that these sensors were much more sensitive in solution compared to most of the existing small‐molecule fluorescence chemosensors based on pyrene, triphenylene, triphenylamine, and triazatruxene skeletons. Fluorescence quenching showed that the sensors adsorbed on paper were sensitive to explosives in the solid, solution, and vapor phases, with fast response times of about 10 s. Moreover, these chemosensors are reusable for the detection of nitroaromatic compounds as they recover their fluorescence intensity after quenching.
Controllable direct C-H arylation with high regioselectivity is highly desirable yet remains a formidable challenge. Herein, a facile regioselective direct C-H arylation is developed for efficient construction of a variety of symmetrical dithienophthalimide-based π-conjugated molecules. The resulting methodology is applicable to a wide range of substrates, from electron-rich units to electron-deficient units with large steric end groups. Aryl halides have been confirmed to be able to couple with dithienophthalimide (DTI) via direct C-H arylation, showing high regioselectivity. Varying the functional end groups onto the DTI core has been demonstrated to fine tune the emission colors to cover most of the visible spectra. The results suggest a facile strategy towards highly selective direct C-H arylation, opening the prospects towards efficient construction of π-conjugated molecules for various potential optoelectronic applications.
Au niquep lanar and highly p-extended scaffold, 3,8,14,, was synthesized via af acile one-pots trategy.T he structure of 4Br-DIT was adequately verified by MALDI-TOFm ass spectrometry, 1 Ha nd 13 CNMR, and single-crystal XRD analysis. Ac ombination of thermal, optical, and electrochemical investigation confirmed the electron-richc haracteristics of the resulting diindolotriazatruxene unit, showingp romise as ab uilding block to construct highly p-extended polycyclic aromatic hydrocarbons (PAHs).
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