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 ChemistryThe Hebrew University of Jerusalem
Shenkar, 23/12/2014
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1. Why is a chemist visiting Shenkar’s design department?
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Insulin
Haemoglobin
Quasi-crystals
Diffusion-reaction pattern
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Symmetry - a universal language of shape and structure
Mirror symmetry
Rotational symmetry
Rotational and mirror symmetries combined
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Our focus: Mirror symmetry
Called also reflection symmetry, bilateral symmetry
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Why is this symmetry called “mirror symmetry”?
Combining an object with its mirror reflection produces that symmetry
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Combining an object with its mirror reflection produces mirror symmetry
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2D mirror symmetry in chemistry
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3D molecular mirror symmetry
Zeolite
Carbon nanotube
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Alexander McQueen(1969 – 2010)
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2D-Mirror symmetry, textile: scarves design
Alexander McQueen
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The basic 3D mirror symmetry in textile design for fashion
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3D mirror symmetry of the body preserved in textile design
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2. Moving away from mirror symmetry - chirality
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Near symmetry in chemistry
cyclohexane
HIV Protease
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Near-symmetry in McQueen’s design
Bjork
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Far-away from mirror symmetry
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Far-away from mirror symmetry – because of design
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Far-away from mirror symmetry – because of body posture
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Far-away from mirror symmetry – because of body posture and design
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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.
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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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Chirality is an extremely important property in the natural sciences
Life is based on left-handed amino acids and right-handed sugars
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Why is it so important?
To understand it let us take the case of spiral chirality
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Diastereomeric (DS) interactions
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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
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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
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“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)
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Left-handed and right-handed molecules:
*Taste differently
*Smell differently
*Can heal or kill (Thalidomide)
Carvone) R( :Spearmint (S): Caraway
)kummel (
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3. Relevance of chirality considerations to design
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Many textile design patterns are chiral
But now we know that such designs can come in left or right forms; here they are:
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The enantiomeric pair of the same design
Why has McQueen selected the right spiral?
Is it an important question for design?
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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
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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)
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N. Konstom, “Rembrandt’s use of models and mirrors”, BurlingtonMagazine, 99, 94 (1977)
Rembrandt’s 2D-chiral preferences
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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.
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4. Additional considerations in brief
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Induction of chirality: Accessories
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Induction of chirality by 3D texture
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Alexander McQueen
Illumination induces chirality
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Randomness is always a source of chirality
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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?
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Chirality has a degree
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The environment strongly affects perception
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Posture and design - The four possibilities:
# Left design – Left posture
# Left design – Right posture
# Right design – Left posture
# Right design – Right posture
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Diastereomeric interactions with artificial chiral environments
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Diastereomeric interactions with natural chiral environments
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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.