On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry...

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On left and right : Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014

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Page 1: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

On left and right:Symmetry and Chirality in Molecules and Design

David Avnir

Institute of ChemistryThe Hebrew University of Jerusalem

 

Shenkar, 23/12/2014

Page 2: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

1. Why is a chemist visiting Shenkar’s design department?

Page 3: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 4: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Insulin

Haemoglobin

Quasi-crystals

Diffusion-reaction pattern

Page 5: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Symmetry - a universal language of shape and structure

Mirror symmetry

Rotational symmetry

Rotational and mirror symmetries combined

Page 6: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Our focus: Mirror symmetry

Called also reflection symmetry, bilateral symmetry

Page 7: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Why is this symmetry called “mirror symmetry”?

Combining an object with its mirror reflection produces that symmetry

Page 8: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Combining an object with its mirror reflection produces mirror symmetry

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Page 9: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

2D mirror symmetry in chemistry

Page 10: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

3D molecular mirror symmetry

Zeolite

Carbon nanotube

Page 11: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Alexander McQueen(1969 – 2010)

Page 12: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

2D-Mirror symmetry, textile: scarves design

Alexander McQueen

Page 13: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

The basic 3D mirror symmetry in textile design for fashion

Page 14: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

3D mirror symmetry of the body preserved in textile design

Page 15: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

2. Moving away from mirror symmetry - chirality

Page 16: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 17: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 18: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 19: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 20: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 21: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Near symmetry in chemistry

cyclohexane

HIV Protease

Page 22: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Near-symmetry in McQueen’s design

Bjork

Page 23: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Far-away from mirror symmetry

Page 24: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Far-away from mirror symmetry – because of design

Page 25: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Far-away from mirror symmetry – because of body posture

Page 26: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Far-away from mirror symmetry – because of body posture and design

Page 27: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Chirality and handedness

When mirror symmetry is removed, a special property emerges :The object may come in two forms:

a left-form and a right-form (handedness)

*These left and right forms are called enantiomers

*Enantiomers are different objects ,but they look very similar .

The similarity is because they aremirror-images of each other

The difference is that theycannot coincide with each other.

Page 28: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

If there is mirror symmetry, the object coincides with its mirror image, the object is achiral – and there is no pair of enantiomers

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Page 29: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Chirality is an extremely important property in the natural sciences

Life is based on left-handed amino acids and right-handed sugars

Page 30: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Why is it so important?

To understand it let us take the case of spiral chirality

Page 31: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Diastereomeric (DS) interactions

Page 32: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

The hand-glove interactions

The interaction between a right-hand (Rh) and a right-glove (Rg) is different from the interaction of a right-hand (Rh) with a left-glove (Lg)

Two different interactions :

Rh-Rg Rh-Lg

Comfortable vs. Very awkward

Page 33: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

In the life-sciences chiral interactions are highly important

Reason: All biological receptors are chiral; therefore:

The interaction: Left-molecule receptorand the interaction: Right-molecule receptorare different

Page 34: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

“How would you like to live in a Looking-glass House, Kitty? I wonder if they'd give you milk, there? Perhaps Looking-glass milk isn't good to drink“

“Through the Looking Glasss, and What Alice Found There”, Lewis Carrol (1871)

Page 35: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Left-handed and right-handed molecules:

*Taste differently

*Smell differently

*Can heal or kill (Thalidomide)

Carvone) R( :Spearmint (S): Caraway

)kummel (

Page 36: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

3. Relevance of chirality considerations to design

Page 37: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Many textile design patterns are chiral

But now we know that such designs can come in left or right forms; here they are:

Page 38: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

The enantiomeric pair of the same design

Why has McQueen selected the right spiral?

Is it an important question for design?

Page 39: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Our biological receptor at focus :The chiral brain

*The left and right hemispheres of the brain are very unequal

*Therefore, no mirror symmetry – the brain is chiral

*Specifically: the brain is a chiral information receptor

*Therefore, if the information – visual – is chiral, DS interactions result between the brain and the information Therefore, left and right

objects must be perceived differently by the brain

Page 40: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Psychology of aesthetic perception

“ When some pictures are mirror reversed, aesthetic evaluations of them change dramatically”.

“When a painting is viewed in a mirror… even the meaning can change”…

“The first major finding… was that paintings containing left-to-right directional cues were preferred ”…

A. M. Mead and J. P. McLaughlin, Brain and Cognition, 20, 300 (1992)

Page 41: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.
Page 42: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

N. Konstom, “Rembrandt’s use of models and mirrors”, BurlingtonMagazine, 99, 94 (1977)

Rembrandt’s 2D-chiral preferences

Page 43: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Are chirality considerations relevant/important to textile design ?

First answer:

Yes, the left enantiomer and the right enantiomer of the same design may be perceived aesthetically in a different way.

Page 44: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

4. Additional considerations in brief

Page 45: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Induction of chirality: Accessories

Page 46: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Induction of chirality by 3D texture

Page 47: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Alexander McQueen

Illumination induces chirality

Page 48: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Randomness is always a source of chirality

Page 49: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

The specific label is not important :Handedness labeling is an agreed convention, not an

inherent property like chirality itself

Are these left- or right-handed?

Page 50: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Chirality has a degree

Page 51: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

The environment strongly affects perception

Page 52: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Posture and design - The four possibilities:

# Left design – Left posture

# Left design – Right posture

# Right design – Left posture

# Right design – Right posture

Page 53: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Diastereomeric interactions with artificial chiral environments

Page 54: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Diastereomeric interactions with natural chiral environments

Page 55: On left and right: Symmetry and Chirality in Molecules and Design David Avnir Institute of Chemistry The Hebrew University of Jerusalem Shenkar, 23/12/2014.

Conclusion

Are chirality considerations relevant to design?

First answer :Yes, the left enantiomer and the right enantiomer of the same design may be perceived aesthetically in a different way.

Second answer :

Yes - most environments are chiral, and therefore left- and right versions of the same design, interact with it differently.


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Charm, My Final Project, Shenkar Collage

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The chirality of the SiO 4 building block in materials David Avnir Institute of Chemistry, The Hebrew University, Jerusalem Special Symposium on Chemistry.

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CHIRALITY - WMCTC

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