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they had identical reacting groups and underwent the same disulfide
bond formation (Scheme 5.10). If there were no molecular codes,
the two building blocks
would be mixed indistinguishably
and statistically in the reaction products. Convincingly, only the
homoreaction products
1I
and
1J
, identically formed
in the separate homogeneous reactions, could be isolated; no
crosstalk product such as heterogeneous ring compound
1
,
2A
,
2 x 2
, and
2B
was
detected, no matter how early or late the reaction was quenched.
The heterogeneous reaction mixture proceeded as if the reactions
had occurred in separate flasks, demonstrating that the molecular
codes determined by the differently twisted structures effectively
direct the reaction products. Therefore, self-assembly, not a random
collision mechanism, dominates the reaction course.
2C
Independent Codes
S
S
S
S
S
O
S
O S
S
O S
SAc
O
O
SAc
S
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
N
O
O
O
N
O
O
O
N
O
O O
N
O O
N
O
O
N
O
O O
N
O
O
N
N
N
O
O
N
O
O
O
O O
N
O
O
N
a
O
a
Cl
Cl
Cl
S
Cl
Cl
Cl
Cl
Cl
Cl
+
Cl
Cl
+
+
Cl
Cl
+
Cl
Cl
Cl
S
O
N
O
O
N
O
O
O
N
O
O
N
O
O
N
O
O
O
N
O
O
N
O
O
N
O
N
O
O
O
N
O
N
O
O
O
O
N
O
O
O
N
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
SAc
S
O
O
S
SAc
S
O
S
1
2A
1 I
1J
O
2B
2C
2x2
S
O
S
S
S
S
S
Redundant Codes
S
S
S
SAc
SAc
S
S
O
S
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
N
O
O
N
O
O
O
N
O
N
O
O
N
a
O
N
O
O
a
O
N
O
O
N
O
+
S
S
+
S
S
O
N
O
O
N
O
O
N
+ monocyclic
and catenated
products
O
N
O
O
O
N
O
N
O
O
O
O
N
O
O
N
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
SAc
O
O
SAc
O
O
1K
O
1 I
S
O
2I
2J
2A
S
S
S
O
S
S
Scheme 5.10
Reaction between independently coded monomers
1I
and
1J
results in homochromophoric products
1
,
2A
,
2 x 2
, and
2B
only, the identical products observed in homogeneous
reactions in separate flasks. No heterochromophoric
cyclic product
was isolated. However, reaction between
redundantly coded planar monomers
2C
1I
and
1K
resulted
in a new heterochromophoric compound
2J
, manifesting
crosstalk between compatible codes.
a
: NaOMe, CH
Cl
, air;
2
2
H + quench.
 
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