Unraveling the unusual effect of fluorination on crystal packing in an organic semiconductor

2020 ◽  
Vol 22 (3) ◽  
pp. 1665-1673 ◽  
Author(s):  
Ekaterina A. Komissarova ◽  
Dmitry I. Dominskiy ◽  
Vladimir E. Zhulanov ◽  
George G. Abashev ◽  
Afzal Siddiqui ◽  
...  
Keyword(s):  
Organic Semiconductor ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Molecular Packing ◽  
Pi Stacking ◽  
Unusual Effect ◽  
Naphthalene Diimide

Two-atom variation in the chemical structure of a naphthalene diimide derivative induced an unexpected crossover from pi-stacking to herringbone molecular packing.

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).

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>

The impact of chemical structure and molecular packing on the electronic polarisation of fullerene arrays

2017 ◽  
Vol 19 (28) ◽  
pp. 18709-18720 ◽  
Author(s):  
Sheridan Few ◽  
Cleaven Chia ◽  
Daniel Teo ◽  
James Kirkpatrick ◽  
Jenny Nelson
Keyword(s):  
Charge Separation ◽  
Chemical Structure ◽  
Molecular Packing ◽  
Large Influence ◽  
The Impact

Calculations show that molecular packing motif and direction of separation have a large influence on the energetic landscape for charge separation in fullerene arrays.

Enhancement in Room Temperature Ammonia Sensing Properties of Naphthalene Diimides through Core Expansion

2022 ◽  
Author(s):  
Salman Ali ◽  
Mohammed Jameel ◽  
Glenn Oldham ◽  
Akhil Gupta ◽  
Mahnaz Shafiei ◽  
...  
Keyword(s):  
Active Layer ◽  
Organic Semiconductor ◽  
Room Temperature ◽  
Ammonia Gas ◽  
Sensing Properties ◽  
Ammonia Sensing ◽  
Naphthalene Diimide ◽  
Naphthalene Diimides

An amperometric type sensor whose active layer is derived from a tetra core-substituted organic semiconductor, naphthalene diimide (NDI-CN4), has been evaluated for ammonia gas (3, 6, 25 and 50 ppm)...

Uncovering the unusual effect of halogenation on crystal packing in an azzaacee-based electron transporting material

2021 ◽  
Vol 259 ◽  
pp. 124060
Author(s):  
Jiwei Tang ◽  
Yan Zhang ◽  
Youcheng Qin ◽  
Kai Ren ◽  
Rongxing He ◽  
...  
Keyword(s):  
Crystal Packing ◽  
Unusual Effect

1-aminoanthraquinone: Crystal data and a model of molecular packing

1998 ◽  
Vol 13 (2) ◽  
pp. 85-88 ◽  
Author(s):  
A. V. Yatsenko ◽  
V. V. Chernyshev ◽  
L. A. Aslanov ◽  
H. Schenk
Keyword(s):  
Powder Diffraction ◽  
Diffraction Data ◽  
Crystal Packing ◽  
Molecular Packing ◽  
Inversion Center ◽  
Crystal Data ◽  
Powder Diffraction Data ◽  
Special Position ◽  
Cell Parameters ◽  
Packing Model

The powder diffraction data for 1-aminoanthraquinone at 295 K (P1¯, No. 2, Z=1) are given. The cell parameters found are a=8.205(1), b=8.396(1), c=3.7882(3) Å, α=93.46(1), β=92.57(1), γ=105.13(1)°. The crystal packing model is proposed giving Rb=0.095. The disordered molecule of 1-aminoanthraquinone occupies a special position on the inversion center.

scholarly journals Organic Semiconductor-Containing Supramolecules: Effect of Small Molecule Crystallization and Molecular Packing

2016 ◽  
Vol 49 (3) ◽  
pp. 833-843 ◽  
Author(s):  
Benjamin J. Rancatore ◽  
BongSoo Kim ◽  
Clayton E. Mauldin ◽  
Jean M. J. Fréchet ◽  
Ting Xu
Keyword(s):  
Small Molecule ◽  
Organic Semiconductor ◽  
Molecular Packing

The Relation Between Molecular Packing or Morphology and Chemical Structure or Processing Conditions: the Effect on Electronic Properties

2014 ◽  
Vol 24 (17) ◽  
pp. 2530-2536 ◽  
Author(s):  
Pramod Kumar ◽  
Kammasandra Nanajunda Shivananda ◽  
Wojciech Zajączkowski ◽  
Wojciech Pisula ◽  
Yoav Eichen ◽  
...  
Keyword(s):  
Electronic Properties ◽  
Chemical Structure ◽  
Molecular Packing ◽  
Processing Conditions

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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