Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

Takashi Takeda; Tomoyuki Akutagawa

doi:10.1002/chem.201600794

Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

Takashi Takeda, Tomoyuki Akutagawa

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

Ethylacridone (1 b) and dicyanomethylenated acridones 2 a,b,d showed crystal-jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable-temperature X-ray crystal-structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2.

Original language	English
Pages (from-to)	7763-7770
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	23
DOIs	https://doi.org/10.1002/chem.201600794
Publication status	Published - 2016 Jun 1

Keywords

acridones
crystal growth
molecular motion
structure-activity relationships
thermosalient effects

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201600794

Cite this

@article{386cf1a3b470412bb9cff68ffb6078bf,

title = "Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives",

abstract = "Ethylacridone (1 b) and dicyanomethylenated acridones 2 a,b,d showed crystal-jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable-temperature X-ray crystal-structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2.",

keywords = "acridones, crystal growth, molecular motion, structure-activity relationships, thermosalient effects",

author = "Takashi Takeda and Tomoyuki Akutagawa",

year = "2016",

month = jun,

day = "1",

doi = "10.1002/chem.201600794",

language = "English",

volume = "22",

pages = "7763--7770",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "23",

}

TY - JOUR

T1 - Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

AU - Takeda, Takashi

AU - Akutagawa, Tomoyuki

PY - 2016/6/1

Y1 - 2016/6/1

N2 - Ethylacridone (1 b) and dicyanomethylenated acridones 2 a,b,d showed crystal-jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable-temperature X-ray crystal-structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2.

AB - Ethylacridone (1 b) and dicyanomethylenated acridones 2 a,b,d showed crystal-jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable-temperature X-ray crystal-structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2.

KW - acridones

KW - crystal growth

KW - molecular motion

KW - structure-activity relationships

KW - thermosalient effects

UR - http://www.scopus.com/inward/record.url?scp=84964659747&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84964659747&partnerID=8YFLogxK

U2 - 10.1002/chem.201600794

DO - 10.1002/chem.201600794

M3 - Article

AN - SCOPUS:84964659747

VL - 22

SP - 7763

EP - 7770

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 23

ER -

Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this