Synthesis of multi‐porphyrin arrays and study of their self‐assembly behaviour at the air–water interface

Abstract

A series of multi‐porphyrin arrays were synthesized and the self‐assembly behaviour of these compounds at the air–water interface was investigated by the Langmuir–Blodgett technique. It was found that as the overall area of the porphyrin molecules was increased, upon going from a mono‐ to bis‐ to a tetra‐ and then to hexaporphyrin species, the intermolecular stacking between the molecules also increases, resulting in more stable monolayers. In the case of the hexaporphyrin species the intermolecular interactions are so strong that monolayer formation is irreversible. All porphyrin monolayers can be transferred to a glass surface with good transfer ratios, leading to highly ordered porphyrin films in which the chromophores are arranged orthogonal to the glass surface. Copyright © 2001 John Wiley & Sons, Ltd.

Helical Polymer‐Anchored Porphyrin Nanorods

“…4‐(Dodecyloxy)benzaldehyde (3) : This compound was synthesized using a modified literature procedure, that is dodecyl bromide was used instead of hexadecyl bromide in cyclohexanone 23 . 1 H NMR (CDCl 3 , 300.13 MHz): δ =9.88 (s, 1 H; HC(O)), 7.82 (d, 2 H; ArH ortho to formyl), 6.98 (d, 2 H; ArH ortho to formyl), 4.04 (t, 2 H; OCH 2 ), 1.81 (p(pentet), 2 H; OCH 2 CH 2 ), 1.46 (p, 2 H; OCH 2 CH 2 OCH 2 ), 1.27 (m, 16 H; aliphatic), 0.88 (t, 3 H; CH 3 ).…”

Metal-Mediated Multi-Porphyrin Discrete Assembliesand Their Photoinduced Properties

“…The adducts in which the two mono-pyridyl porphyrins bear long 4-hexadecyloxyl chains at the para positions of the meso phenyl groups were also assembled into stable monolayers on a water surface [59].…”

“…With a similar synthetic approach, Drain and co-workers prepared also more elaborate architectures, such as linear trimers, tapes and tessellated [49] and [59]) [53] and [54]) arrays of porphyrins by one-pot self-assembly of different metal precursors and/or porphyrin building blocks [50]. For example, the molecular tape shown in Fig.…”

“…4) and the host-guest complex was also structurally characterized in the solid state by X-ray crystallography [61]. 4 ], respectively [59,74] 2 (Fig. 5).…”

“…The angular connectors employed 3 Schematic drawing of the square planar and octahedral metal fragments (and of their precursors) most commonly used in the metal-driven construction of multiporphyrin assemblies so far are relatively few ( Fig. 3 4 ] (X = Cl, Br) have been used as cruciform fragments since they can provide four coplanar coordination sites [51,59].…”