π-Depletion as a criterion to predict π-stacking ability

被引：86

作者：

Gonthier, Jerome F. ^{[1
]}

Steinmann, Stephan N. ^{[1
]}

Roch, Loic ^{[1
]}

Ruggi, Albert ^{[1
]}

Luisier, Nicolas ^{[1
]}

Severin, Kay ^{[1
]}

Corminboeuf, Clemence ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne EPFL, Inst Sci & Ingn Chim, Lausanne, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 74期

基金：

瑞士国家科学基金会;

关键词：

AROMATIC RINGS; DENSITY; SANDWICH; NICS;

D O I：

10.1039/c2cc33886f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The screening of molecular targets benefits from design criteria, which can identify the most promising candidates. We demonstrate that pi-depleted polyaromatic molecules present superior pi-stacking ability. This realization is quantified using a computational criterion, LOLIPOP, that detects ideal pi-conjugated frameworks. The utility of LOLIPOP is illustrated by identifying tailored chemosensors.

引用

页码：9239 / 9241

页数：3

共 20 条

[1] Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].

Adamo, C ;

Barone, V .

JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170

[2] Taking the Aromaticity out of Aromatic Interactions [J].

Bloom, Jacob W. G. ;

Wheeler, Steven E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (34) :7847-7849

[3] Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].

Chen, ZF ;

Wannere, CS ;

Corminboeuf, C ;

Puchta, R ;

Schleyer, PV .

CHEMICAL REVIEWS, 2005, 105 (10) :3842-3888

[4] DOMINANCE OF POLAR/PI OVER CHARGE-TRANSFER EFFECTS IN STACKED PHENYL INTERACTIONS [J].

COZZI, F ;

CINQUINI, M ;

ANNUZIATA, R ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5330-5331

[5] Which NICS aromaticity index for planar π rings is best? [J].

Fallah-Bagher-Shaidaei, H ;

Wannere, CS ;

Corminboeuf, C ;

Puchta, R ;

Schleyer, PV .

ORGANIC LETTERS, 2006, 8 (05) :863-866

[6] Origin of the Surprising Enhancement of Electrostatic Energies by Electron-Donating Substituents in Substituted Sandwich Benzene Dimers [J].

Hohenstein, Edward G. ;

Duan, Jiana ;

Sherrill, C. David .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13244-13247

[7] Effects of Heteroatoms on Aromatic π-π Interactions: Benzene-Pyridine and Pyridine Dimer [J].

Hohenstein, Edward G. ;

Sherrill, C. David .

JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (05) :878-886

[8] THE NATURE OF PI-PI INTERACTIONS [J].

HUNTER, CA ;

SANDERS, JKM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5525-5534

[9] PERTURBATION-THEORY APPROACH TO INTERMOLECULAR POTENTIAL-ENERGY SURFACES OF VAN-DER-WAALS COMPLEXES [J].

JEZIORSKI, B ;

MOSZYNSKI, R ;

SZALEWICZ, K .

CHEMICAL REVIEWS, 1994, 94 (07) :1887-1930

[10] A ratiometric fluorescence sensor for caffeine [J].

Luisier, Nicolas ;

Ruggi, Albert ;

Steinmann, Stephan N. ;

Favre, Laurane ;

Gaeng, Nicolas ;

Corminboeuf, Clemence ;

Severin, Kay .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (37) :7487-7490

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