1519006-19-9

Upstream product

• 1519006-16-6 4,7-diiodoindan-1,3-dione 
• 1519006-17-7 2-[4-(N,N-dimethylamino)benzylidene]-4,7-diiodoindan-1,3-dione 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 35046-80-1 3,6-diiodophthalanhydride 

Relevant academic research and scientific papers

T-Shaped (Donor-π-)2Acceptor-π-Donor Push-Pull Systems Based on Indan-1,3-dione

Sixteen model (donor-π-)2acceptor-π-donor [(D-π-)2A-π-D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push-pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all target molecules were investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed, and structure-property relationships were evaluated. Electron donors attached at the C-2 position through π systems of various lengths affect the studied properties most significantly. The side donors at C-4 and C-7 can be described as auxiliary and do not dominate the observed properties. However, thiophene is a more efficient donor than N,N-dimethylaniline in this respect. Hence, indan-1,3-dione bearing a piperidylthiophene donor connected through a propenylidene spacer at C-2 completed with two side thiophen-2-ylethynyl branches at C-4 and C-7 showed the highest figure of merit among the studied properties. T-shaped chromophores based on an indan-1,3-dione central acceptor with systematically varied peripheral donors are investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry (DSC), electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. Structure-property relationships are subsequently elucidated.

T-shaped push-pull chromophores: First modification of the indan-1,3-dione-fused benzene ring by cross-coupling reactions

A series of eight novel T-shaped chromophores with indan-1,3-dione central acceptor moiety and peripheral N,N-dimethylamino and thiophene donors were synthesized. 4,7-Diiodoindan-1,3-dione was prepared in a straightforward manner from phthalanhydride. Its modification with donors was accomplished by Knoevenagel, Suzuki-Miyaura, and Sonogashira reactions. Target push-pull chromophores were further investigated by X-ray analysis, UV/Vis spectra, and theoretical calculations. Georg Thieme Verlag Stuttgart, New York.