Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative

Simon Kervyn De Meerendre, Oliver Fenwick, Francesco Di Stasio, Yong Sig Shin, Johan Wouters, Gianluca Accorsi, Silvio Osella, David Beljonne, Franco Cacialli, Davide Bonifazi

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

We have prepared a new borazine derivative that bears mesityl substituents at the boron centers and displays exceptional chemical stability. Detailed crystallographic and solid-state fluorescence characterizations revealed the existence of several polymorphs, each of which showed different emission profiles. In particular, a bathochromic shift is observed when going from the lower- to the higher-density crystal. Computational investigations of the conformational dynamics of borazine 1 in both the gas phase and in the solid state using molecular dynamics (MD) simulations showed that the conformation of the peripheral aryl groups significantly varies when going from an isolated molecule (in which the rings are able to flip over the 90° barrier at RT) to the crystals (in which the rotation is locked by packing effects), thus generating specific nonsymmetric intermolecular interactions in the different polymorphs. To investigate the optoelectronic properties of these materials by fabrication and characterization of light-emitting diodes (LEDs) and light-emitting electrochemical cells (LECs), borazine 1 was incorporated as the active material in the emissive layer. The current and radiance versus voltage characteristics, as well as the electroluminescence spectra reported here for the first time are encouraging prospects for the engineering of future borazine-based devices.

langue originaleAnglais
Pages (de - à)7771-7779
Nombre de pages9
journalChemistry: A European Journal
Volume19
Numéro de publication24
Les DOIs
étatPublié - 10 juin 2013

Empreinte digitale

Polymorphism
Optoelectronic devices
Fluorescence
Derivatives
Crystals
Electrochemical cells
Chemical stability
Electroluminescence
Light emitting diodes
Boron
Conformations
Molecular dynamics
Display devices
Fabrication
Molecules
Computer simulation
Electric potential
Gases
borazine

Citer ceci

Kervyn De Meerendre, Simon ; Fenwick, Oliver ; Di Stasio, Francesco ; Shin, Yong Sig ; Wouters, Johan ; Accorsi, Gianluca ; Osella, Silvio ; Beljonne, David ; Cacialli, Franco ; Bonifazi, Davide. / Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative. Dans: Chemistry: A European Journal. 2013 ; Vol 19, Numéro 24. p. 7771-7779.
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title = "Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative",
abstract = "We have prepared a new borazine derivative that bears mesityl substituents at the boron centers and displays exceptional chemical stability. Detailed crystallographic and solid-state fluorescence characterizations revealed the existence of several polymorphs, each of which showed different emission profiles. In particular, a bathochromic shift is observed when going from the lower- to the higher-density crystal. Computational investigations of the conformational dynamics of borazine 1 in both the gas phase and in the solid state using molecular dynamics (MD) simulations showed that the conformation of the peripheral aryl groups significantly varies when going from an isolated molecule (in which the rings are able to flip over the 90° barrier at RT) to the crystals (in which the rotation is locked by packing effects), thus generating specific nonsymmetric intermolecular interactions in the different polymorphs. To investigate the optoelectronic properties of these materials by fabrication and characterization of light-emitting diodes (LEDs) and light-emitting electrochemical cells (LECs), borazine 1 was incorporated as the active material in the emissive layer. The current and radiance versus voltage characteristics, as well as the electroluminescence spectra reported here for the first time are encouraging prospects for the engineering of future borazine-based devices.",
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author = "{Kervyn De Meerendre}, Simon and Oliver Fenwick and {Di Stasio}, Francesco and Shin, {Yong Sig} and Johan Wouters and Gianluca Accorsi and Silvio Osella and David Beljonne and Franco Cacialli and Davide Bonifazi",
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Kervyn De Meerendre, S, Fenwick, O, Di Stasio, F, Shin, YS, Wouters, J, Accorsi, G, Osella, S, Beljonne, D, Cacialli, F & Bonifazi, D 2013, 'Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative', Chemistry: A European Journal, VOL. 19, Numéro 24, p. 7771-7779. https://doi.org/10.1002/chem.201204598

Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative. / Kervyn De Meerendre, Simon; Fenwick, Oliver; Di Stasio, Francesco; Shin, Yong Sig; Wouters, Johan; Accorsi, Gianluca; Osella, Silvio; Beljonne, David; Cacialli, Franco; Bonifazi, Davide.

Dans: Chemistry: A European Journal, Vol 19, Numéro 24, 10.06.2013, p. 7771-7779.

Résultats de recherche: Contribution à un journal/une revueArticle

TY - JOUR

T1 - Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative

AU - Kervyn De Meerendre, Simon

AU - Fenwick, Oliver

AU - Di Stasio, Francesco

AU - Shin, Yong Sig

AU - Wouters, Johan

AU - Accorsi, Gianluca

AU - Osella, Silvio

AU - Beljonne, David

AU - Cacialli, Franco

AU - Bonifazi, Davide

PY - 2013/6/10

Y1 - 2013/6/10

N2 - We have prepared a new borazine derivative that bears mesityl substituents at the boron centers and displays exceptional chemical stability. Detailed crystallographic and solid-state fluorescence characterizations revealed the existence of several polymorphs, each of which showed different emission profiles. In particular, a bathochromic shift is observed when going from the lower- to the higher-density crystal. Computational investigations of the conformational dynamics of borazine 1 in both the gas phase and in the solid state using molecular dynamics (MD) simulations showed that the conformation of the peripheral aryl groups significantly varies when going from an isolated molecule (in which the rings are able to flip over the 90° barrier at RT) to the crystals (in which the rotation is locked by packing effects), thus generating specific nonsymmetric intermolecular interactions in the different polymorphs. To investigate the optoelectronic properties of these materials by fabrication and characterization of light-emitting diodes (LEDs) and light-emitting electrochemical cells (LECs), borazine 1 was incorporated as the active material in the emissive layer. The current and radiance versus voltage characteristics, as well as the electroluminescence spectra reported here for the first time are encouraging prospects for the engineering of future borazine-based devices.

AB - We have prepared a new borazine derivative that bears mesityl substituents at the boron centers and displays exceptional chemical stability. Detailed crystallographic and solid-state fluorescence characterizations revealed the existence of several polymorphs, each of which showed different emission profiles. In particular, a bathochromic shift is observed when going from the lower- to the higher-density crystal. Computational investigations of the conformational dynamics of borazine 1 in both the gas phase and in the solid state using molecular dynamics (MD) simulations showed that the conformation of the peripheral aryl groups significantly varies when going from an isolated molecule (in which the rings are able to flip over the 90° barrier at RT) to the crystals (in which the rotation is locked by packing effects), thus generating specific nonsymmetric intermolecular interactions in the different polymorphs. To investigate the optoelectronic properties of these materials by fabrication and characterization of light-emitting diodes (LEDs) and light-emitting electrochemical cells (LECs), borazine 1 was incorporated as the active material in the emissive layer. The current and radiance versus voltage characteristics, as well as the electroluminescence spectra reported here for the first time are encouraging prospects for the engineering of future borazine-based devices.

KW - boron

KW - doping

KW - molecular modeling

KW - nitrogen

KW - polymorphism

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U2 - 10.1002/chem.201204598

DO - 10.1002/chem.201204598

M3 - Article

AN - SCOPUS:84878557730

VL - 19

SP - 7771

EP - 7779

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 24

ER -