Polyhalogenated aminobenzonitriles vs their co-crystals with 18-crown-6: amino group position as a tool to control crystal packing and solid-state fluorescence

CrystEngComm ◽  
2022 ◽  
Author(s):  
Tamara Vaganova ◽  
Enrico Benassi ◽  
Yuri V Gatilov ◽  
Igor P. Chuikov ◽  
Denis P Pishchur ◽  
...  
Keyword(s):  
Solid State ◽  
Supramolecular Structure ◽  
Crystal Packing ◽  
Amino Group ◽  
Group Position ◽  
Solid State Fluorescence

A series of para- and ortho-aminobenzonitriles differing in the nature and number of halogen substituents was used to synthesize 2:1 co-crystals with 18-crown-6 ether. Supramolecular structure of the obtained co-crystals...

Impact of molecular packing rearrangement on solid-state fluorescence: polyhalogenated N-hetarylamines vs. their co-crystals with 18-crown-6

CrystEngComm ◽  
2019 ◽  
Vol 21 (39) ◽  
pp. 5931-5946 ◽  
Author(s):  
Tamara A. Vaganova ◽  
Yurij V. Gatilov ◽  
Enrico Benassi ◽  
Igor P. Chuikov ◽  
Denis P. Pishchur ◽  
...  
Keyword(s):  
Solid State ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Molecular Packing ◽  
Solid State Fluorescence

Relationship between the hetarylamine chemical structure, crystal packing in homo- and co-crystals, and fluorescence effects (quenching, bathochromic and hypsochromic shifts).

scholarly journals Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides

2012 ◽  
Vol 8 ◽  
pp. 266-274 ◽  
Author(s):  
Kenichirou Yokota ◽  
Masayori Hagimori ◽  
Naoko Mizuyama ◽  
Yasuhisa Nishimura ◽  
Hiroshi Fujito ◽  
...  
Keyword(s):  
Solid State ◽  
Quantum Chemical ◽  
Computational Analysis ◽  
Pyrimidine Ring ◽  
Amino Group ◽  
Pyrimidine Derivatives ◽  
Ketene Dithioacetals ◽  
Solid State Fluorescence ◽  
Guanidine Carbonate ◽  
Fluorescent Compounds

New fluorescent compounds, benzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides (3a–g), 2-amino-4-methylsulfanylbenzo[4,5]thieno[3,2-d]pyrimidine (6), and 2-amino-4-methylsulfanyl-7-methoxybenzo[4,5]furo[3,2-d]pyrimidine (7), were synthesized in good yields from heterocyclic ketene dithioacetals (1a–c) and guanidine carbonate (2a) or (S)-methylisothiourea sulfate (2b) in pyridine under reflux. Among the fused pyrimidine derivatives, compound 3c, which has an amino group at the 2-position and a benzylamino group at the 4-position of the pyrimidine ring, showed the strongest solid-state fluorescence. The absorption and emission properties of the compounds were quantitatively reproduced by a series of ab initio quantum-chemical calculations.

Synthesis and solid-state fluorescence properties of pentacyclic 7-substituted-indeno[1′,2′:4,5]pyrido[2,1-a]isoindol-5-ones

RSC Advances ◽  
2015 ◽  
Vol 5 (4) ◽  
pp. 2715-2723 ◽  
Author(s):  
Z. Chamas ◽  
E. Marchi ◽  
B. Presson ◽  
E. Aubert ◽  
Y. Fort ◽  
...  
Keyword(s):  
Solid State ◽  
Crystal Packing ◽  
Fluorescence Properties ◽  
Quantum Yields ◽  
Solid State Fluorescence ◽  
Packing Analysis

New pentacyclic indeno[1′,2′:4,5]pyrido[2,1-a]isoindol-5-ones were designed which possess quantum yields in the solid state up to 32%. The importance of the substituent in 7-position was highlighted through crystal packing analysis.

The Influence of Nitrogen Position on Charge Carrier Mobility in Enantiopure Aza[6]helicene Crystals

2018 ◽  
Author(s):  
Francesco Salerno ◽  
Beth Rice ◽  
Julia Schmidt ◽  
Matthew J. Fuchter ◽  
Jenny Nelson ◽  
...  
Keyword(s):  
Solid State ◽  
Charge Carrier ◽  
Carrier Mobility ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Charge Carrier Mobility ◽  
Individual Factor ◽  
Charge Mobility ◽  
Order Of Magnitude ◽  
Small Change

<p>The properties of an organic semiconductor are dependent on both the chemical structure of the molecule involved, and how it is arranged in the solid-state. It is challenging to extract the influence of each individual factor, as small changes in the molecular structure often dramatically change the crystal packing and hence solid-state structure. Here, we use calculations to explore the influence of the nitrogen position on the charge mobility of a chiral organic molecule when the crystal packing is kept constant. The transfer integrals for a series of enantiopure aza[6]helicene crystals sharing the same packing were analysed in order to identify the best supramolecular motifs to promote charge carrier mobility. The regioisomers considered differ only in the positioning of the nitrogen atom in the aromatic scaffold. The simulations showed that even this small change in the chemical structure has a strong effect on the charge transport in the crystal, leading to differences in charge mobility of up to one order of magnitude. Some aza[6]helicene isomers that were packed interlocked with each other showed high HOMO-HOMO integrals (up to 70 meV), whilst molecules arranged with translational symmetry generally afforded the highest LUMO-LUMO integrals (40 - 70 meV). As many of the results are not intuitively obvious, a computational approach provides additional insight into the design of new semiconducting organic materials.</p>

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