1209009-14-2

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 205877-26-5 4-diphenylaminophenylacetylene 
• 205877-25-4 N,N-diphenyl-4-[(trimethylsilyl)ethynyl]benzenamine 
• 603-34-9 N,N-diphenylaminobenzene 
• 38257-52-2 4-(N,N-diphenylamino)iodobenzene 

Downstream Products

• 1209009-19-7 C₂₉H₂₁NO 
• 1620996-84-0 3-(5-(4-((4-(diphenylamino)phenyl)ethynyl)phenyl)thiophen-2-yl)-2,5-dioctyl-6-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-dione 
• 1620996-85-1 4-(5-{4-[5-(4-{[4-(diphenylamino)phenyl]ethynyl}phenyl)thiophen-2-yl]-2,5-dioctyl-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl}thiophen-2-yl)benzonitrile 
• 1607819-42-0 N-{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]ethynylphenyl}diphenylamine 
• 1332870-01-5 4,5-bis[4-((4-(diphenylamino)phenyl) ethynyl)phenyl]-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene 
• 1332870-00-4 4,6-bis[4-((4-(diphenylamino)phenyl)ethynyl)phenyl]dibenzo[b,d]furan 
• 1332869-99-4 4,6-bis[4-((4-(diphenylamino)phenyl)ethynyl)phenyl]dibenzo[b,d]thiophene 
• 1332869-98-3 1,8-bis[4-((4-(diphenylamino)phenyl)ethynyl)phenyl]naphthalene 
• 1332869-79-0 4-[4-(N,N-diphenylamino)phenylethynyl]phenylboronic acid 

Relevant academic research and scientific papers

Linkage effects of linear D-π-A-π-D type diketopyrrolopyrrole- triphenylamine based solution-processable organic small molecule photovoltaic materials

Four novel D-π-A-π-D-type small molecules (SMs) were synthesized and their π-linkage effects were investigated. Among them, SM2 with vinylene as the π-linkage exhibited better molecular coplanarity, reaching a relatively higher power conversion efficiency (PCE) of 3.76%. SM3 and SM4 with acetylene and acrylonitrile as π-linkages exhibited relatively higher open-circuit voltages (VOC) of 0.93 V and 0.90 V, respectively, owing to their deep-lying HOMO levels. These results gave an important guide for developing new materials in solution-processed small molecule solar cells.

High performance asymmetrical push-pull small molecules end-capped with cyanophenyl for solution-processed solar cells

Two novel asymmetrical push-pull small molecules have been synthesized successfully, consisting of triphenylamine and diketopyrrolopyrrole as a fundamental dipolar D-π-A structure with ethynylbenzene as the π-bridge. TPATDPPCN end-capped with cyanophenyl exhibits a low optical band gap of 1.65 eV, and an impressive PCE of 5.94% has been achieved. This journal is the Partner Organisations 2014.

Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes

A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of β-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH2Cl2, resulting in high quantum yields.

Synthesis and spectroscopic study of phenylenee (poly) ethynylenes substituted by amino or amino/cyano groups at terminal(s):Electronic effect of cyano group on charge-transfer excitation of acetylenic φ-systems

To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic p-systems, phenylenee(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of b-substituted sulfones.These substituted phenyleneethynylenes showed large molar absorption coefficients 3, and emitted strong fluorescence upon UV light irradiation.Phenylenee(poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields FF as their polyethynylene motifs e(C^C)ne expanded.The drastic decrease of fluorescence quantum yields FF were explained in terms of increasing nonradiative reaction rate constants knr, which had been determined by the corresponding fluorescence quantum yields F F and lifetime values s.The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state.Comparison of slope values r in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylenee(poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic p-systems with cyano group did little.