Résumé

N-Salicylideneanilines are interesting model compounds for understanding solid-state photochromism. The introduction of bulky substituents (trityl or tert-butyl groups) by chemical modification of the N-salicylideneaniline derivative is an effective method to build up photochromic solids. Alternatively, we propose, herein, a supramolecular approach to design photochromic materials which involves the introduction of a bulky anion in the structure. In this context, this is the first report on N-salicylideneamino-1-alkylpyridinium salts (iodide and tetraphenylboride salts). Iodide salts were obtained by alkylation of the parent N-salicylideneaminopyridine with the appropriate iodoalkane (iodomethane or iodoethane) in acetone. The iodide salts were used as the starting material for the production of tetraphenylborate salts by anion-exchange in methanol. All solids were characterized by means of X-ray diffraction and absorption spectroscopy. The effect of different counterions as well as the effect of the crystal structure on the solid-state photochromism is investigated.
langue originaleAnglais
Pages (de - à)10999–11007
Nombre de pages9
journalJournal of Physical Chemistry C
Volume122
Numéro de publication20
Les DOIs
étatPublié - 30 avr. 2018

Empreinte digitale

Tetraphenylborate
Photochromism
photochromism
Anions
boxes
Negative ions
Salts
anions
salts
Derivatives
Iodides
iodides
solid state
alkylation
Alkylation
Chemical modification
X ray absorption
Acetone
Absorption spectroscopy
acetone

Citer ceci

@article{5e2c13306b794066b25c791d46b85c88,
title = "Tetraphenylborate Anion Induces Photochromism in N-Salicylideneamino-1-alkylpyridinium Derivatives Through Formation of Tetra-Aryl Boxes",
abstract = "N-Salicylideneanilines are interesting model compounds for understanding solid-state photochromism. The introduction of bulky substituents (trityl or tert-butyl groups) by chemical modification of the N-salicylideneaniline derivative is an effective method to build up photochromic solids. Alternatively, we propose, herein, a supramolecular approach to design photochromic materials which involves the introduction of a bulky anion in the structure. In this context, this is the first report on N-salicylideneamino-1-alkylpyridinium salts (iodide and tetraphenylboride salts). Iodide salts were obtained by alkylation of the parent N-salicylideneaminopyridine with the appropriate iodoalkane (iodomethane or iodoethane) in acetone. The iodide salts were used as the starting material for the production of tetraphenylborate salts by anion-exchange in methanol. All solids were characterized by means of X-ray diffraction and absorption spectroscopy. The effect of different counterions as well as the effect of the crystal structure on the solid-state photochromism is investigated.",
author = "Andrea Carletta and Melwin Cola{\cc}o and S{\'e}bastien Mouchet and Aur{\'e}lie Plas and Nikolay Tumanov and Luca Fusaro and Beno{\^i}t Champagne and Steve Lanners and Johan Wouters",
year = "2018",
month = "4",
day = "30",
doi = "10.1021/acs.jpcc.8b02329",
language = "English",
volume = "122",
pages = "10999–11007",
journal = "Journal of physical chemistry. C",
issn = "1932-7447",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - Tetraphenylborate Anion Induces Photochromism in N-Salicylideneamino-1-alkylpyridinium Derivatives Through Formation of Tetra-Aryl Boxes

AU - Carletta, Andrea

AU - Colaço, Melwin

AU - Mouchet, Sébastien

AU - Plas, Aurélie

AU - Tumanov, Nikolay

AU - Fusaro, Luca

AU - Champagne, Benoît

AU - Lanners, Steve

AU - Wouters, Johan

PY - 2018/4/30

Y1 - 2018/4/30

N2 - N-Salicylideneanilines are interesting model compounds for understanding solid-state photochromism. The introduction of bulky substituents (trityl or tert-butyl groups) by chemical modification of the N-salicylideneaniline derivative is an effective method to build up photochromic solids. Alternatively, we propose, herein, a supramolecular approach to design photochromic materials which involves the introduction of a bulky anion in the structure. In this context, this is the first report on N-salicylideneamino-1-alkylpyridinium salts (iodide and tetraphenylboride salts). Iodide salts were obtained by alkylation of the parent N-salicylideneaminopyridine with the appropriate iodoalkane (iodomethane or iodoethane) in acetone. The iodide salts were used as the starting material for the production of tetraphenylborate salts by anion-exchange in methanol. All solids were characterized by means of X-ray diffraction and absorption spectroscopy. The effect of different counterions as well as the effect of the crystal structure on the solid-state photochromism is investigated.

AB - N-Salicylideneanilines are interesting model compounds for understanding solid-state photochromism. The introduction of bulky substituents (trityl or tert-butyl groups) by chemical modification of the N-salicylideneaniline derivative is an effective method to build up photochromic solids. Alternatively, we propose, herein, a supramolecular approach to design photochromic materials which involves the introduction of a bulky anion in the structure. In this context, this is the first report on N-salicylideneamino-1-alkylpyridinium salts (iodide and tetraphenylboride salts). Iodide salts were obtained by alkylation of the parent N-salicylideneaminopyridine with the appropriate iodoalkane (iodomethane or iodoethane) in acetone. The iodide salts were used as the starting material for the production of tetraphenylborate salts by anion-exchange in methanol. All solids were characterized by means of X-ray diffraction and absorption spectroscopy. The effect of different counterions as well as the effect of the crystal structure on the solid-state photochromism is investigated.

UR - https://pubs.acs.org/doi/abs/10.1021/acs.jpcc.8b02329

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