The novel 1 : 1 donor–acceptor complex, 3,4-dimethoxycinnamic acid–2,4-dinitrocinnamic acid. Crystal engineering, structure, and anomalous lack of solid-state topochemical reactivity

1985 ◽  
pp. 1905-1912 ◽  
Author(s):  
Jagarlapudi A. R. P. Sarma ◽  
Gautam R. Desiraju
Keyword(s):  
Solid State ◽  
Crystal Engineering ◽  
The Novel ◽  
Engineering Structure ◽  
Acceptor Complex ◽  
Acid Crystal ◽  
Donor Acceptor

Solid-state complexes of quinoxaline- and phenazine-N,N′-dioxide donors with tetracyanoethylene. Crystal engineering via donor-acceptor interactions

1997 ◽  
Vol 38 (44) ◽  
pp. 7665-7668 ◽  
Author(s):  
Melinda L. Greer ◽  
Joseph R. Duncan ◽  
Janice L. Duff ◽  
Silas C. Blackstock
Keyword(s):  
Solid State ◽  
Crystal Engineering ◽  
Donor Acceptor

Supramolecular control of organic p/n-heterojunctions by complementary hydrogen bonding

2014 ◽  
Vol 174 ◽  
pp. 297-312 ◽  
Author(s):  
Hayden T. Black ◽  
Huaping Lin ◽  
Francine Bélanger-Gariépy ◽  
Dmitrii F. Perepichka
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Self Assembly ◽  
Structural Control ◽  
Molecular Structures ◽  
Mutual Arrangement ◽  
Donor And Acceptor ◽  
Donor Acceptor

The supramolecular structure of organic semiconductors (OSCs) is the key parameter controlling their performance in organic electronic devices, and thus methods for controlling their self-assembly in the solid state are of the upmost importance. Recently, we have demonstrated the co-assembly of p- and n-type organic semiconductors through a three-point hydrogen-bonding interaction, utilizing an electron-rich dipyrrolopyridine (P2P) heterocycle which is complementary to naphthalenediimides (NDIs) both in its electronic structure and H bonding motif. The hydrogen-bonding-mediated co-assembly between P2P donor and NDI acceptor leads to ambipolar co-crystals and provides unique structural control over their solid-state packing characteristics. In this paper we expand our discussion on the crystal engineering aspects of H bonded donor–acceptor assemblies, reporting three new single co-crystal X-ray diffraction structures and analyzing the different packing characteristics that arise from the molecular structures employed. Particular attention is given toward understanding the formation of the two general motifs observed, segregated and mixed stacks. Co-assembly of the donor and acceptor components into a single, crystalline material, allows the creation of ambipolar semiconductors where the mutual arrangement of p- and n-conductive channels is engineered by supramolecular design based on complementary H bonding.

N-Alkylation of Pyromellitic Diimide: Solid-State Structure of the 1 : 1 N,N′-Diethylpyromellitic Diimide/2,6-Dimethoxynaphthalene Cocrystal

1998 ◽  
Vol 51 (5) ◽  
pp. 441 ◽  
Author(s):  
Darren G. Hamilton ◽  
Daniel E. Lynch ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard ◽  
Jeremy K. M. Sanders
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Crystal Packing ◽  
State Structure ◽  
Solid State Structure ◽  
Acceptor Complex ◽  
Donor Acceptor

N-Alkylation of pyromellitic diimide in the presence of CsF affords N-substituted diimide derivatives that lack the hydrogen-bonding ability of the parent diimide. The solid-state structure of the N,N′-diethylpyromellitic diimide/2,6-dimethoxynaphthalene donor{acceptor complex reveals the influence of removing this hydrogen-bonding ability on the crystal packing.

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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