Alternating Hetero H Aggregation of Different Dyes by Interstrand Stacking from Two DNA–Dye Conjugates

Abstract

Seeing red: Aggregates in which methyl red and naphthyl red moieties are stacked alternately in a DNA duplex have been prepared by hybridization of two DNA–dye conjugates (see picture). A sharp absorption band appears at 478 nm, which is different from that of the individual dyes. A strong CD effect is also induced by the interstrand heterostacking of the dyes.

Covalent Incorporation of Methyl Red Dyes into Double‐Stranded DNA for Their Ordered Clustering

“…By using this method, a hetero cluster of two different and alternating dyes is also easily prepared 23. Because some optical properties, such as nonlinear optical activity, are exhibited only by clustered dyes,24 the present dye cluster may also be applicable as a new DNA probe of high sensitivity.…”

DNA-Multichromophore Systems

“…Using a chiral threoninol linker, Asanuma, Komiyama and coworkers incorporated a variety a chromophores into the DNA duplex, including azobenzene, 126 methyl red, 126 naphthyl red, 126 pyrene (Fig. 1C), N,N-dimethylaniline, 127 4′-methylthioazobenzene, 128 4′-dimethylamino-2-nitroazobenzene, 128 p-methylstilbazole 129 and perylene.…”

“…126 Up to six alternating dyes were incorporated in a controlled and predetermined manner. When spacer groups were added between chromophores, both positive and negative CDs were strongly induced by hybridization, indicating the formation of a right-handed helix, closely resembling natural B-DNA (Fig.…”

Formation of Two Homo‐chromophoric H‐Aggregates in DNA‐Assembled Alternating Dye Stacks

“…For delocalized excitation, a high structural order of the individual chromophores is a prerequisite. [7,[23][24][25][26][27][28][29][30][31][32][33] The formation of chromophore segments that are welldefined with regard to the number and kind of the components is readily controlled by hybridization of complementary strands. [4,[19][20][21][22] DNA has been used as a supramolecular scaffold for the construction of distinct arrays of aromatic dyes.…”