Azo•••phenyl stacking: a persistent self-assembly motif guides the assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals

被引：36

作者：

Bushuyev, Oleksandr S. ^{[1
]}

Tomberg, Anna ^{[1
]}

Vinden, Joanna R. ^{[1
]}

Moitessier, Nicolas ^{[1
]}

Barrett, Christopher J. ^{[1
]}

Friscic, Tomislav ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 10期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

HALOGEN-BOND; MOLECULAR-CRYSTALS; SINGLE-CRYSTALS; HYDROGEN-BOND; CO-CRYSTALS; COCRYSTALS; ISOMERIZATION; DESIGN; LIGHT;

D O I：

10.1039/c5cc08590j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a novel, persistent motif of molecular assembly in photo-mechanical crystals and cocrystals of fluorinated cis-azobenzenes. The azo center dot center dot center dot phenyl stacking, preserved upon either chemical substitution or halogen-bonded cocrystallization, guides the assembly of fluorinated cis-azobenzenes into columnar stacks and drives the formation of crystals with needle-like morphologies optimal for photo-mechanical motion.

引用

页码：2103 / 2106

页数：4

共 54 条

[1] Supramolecular Hierarchy among Halogen-Bond Donors [J].

Aakeroey, Christer B. ;

Baldrighi, Michele ;

Desper, John ;

Metrangolo, Pierangelo ;

Resnati, Giuseppe .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (48) :16240-16247

[2] Competing hydrogen-bond and halogen-bond donors in crystal engineering [J].

Aakeroey, Christer B. ;

Panikkattu, Sheelu ;

Chopade, Prashant D. ;

Desper, John .

CRYSTENGCOMM, 2013, 15 (16) :3125-3136

[3] Controlling Motion at the Nanoscale: Rise of the Molecular Machines [J].

Abendroth, John M. ;

Bushuyev, Oleksandr S. ;

Weiss, Paul S. ;

Barrett, Christopher J. .

ACS NANO, 2015, 9 (08) :7746-7768

[4] Crystal engineering of the composition of pharmaceutical phases.: Do pharmaceutical co-crystals represent a new path to improved medicines? [J].

Almarsson, Ö ;

Zaworotko, MJ .

CHEMICAL COMMUNICATIONS, 2004, (17) :1889-1896

[5] ORGANIC ELECTRONICS Addressing challenges [J].

Anthony, John E. .

NATURE MATERIALS, 2014, 13 (08) :773-775

[6] Azobenzene Photoswitching without Ultraviolet Light [J].

Beharry, Andrew A. ;

Sadovski, Oleg ;

Woolley, G. Andrew .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19684-19687

[7] Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary Hydrogen Bonding [J].

Black, Hayden T. ;

Perepichka, Dmitrii F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (08) :2138-2142

[8] o-Fluoroazobenzenes as Readily Synthesized Photoswitches Offering Nearly Quantitative Two-Way Isomerization with Visible Light [J].

Bleger, David ;

Schwarz, Jutta ;

Brouwer, Albert M. ;

Hecht, Stefan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (51) :20597-20600

[9] Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal [J].

Bolton, Onas ;

Matzger, Adam J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8960-8963

[10] VAN DER WAALS VOLUMES + RADII [J].

BONDI, A .

JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+

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