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Abstract

Macrodiscotic materials are liquid crystalline systems composed of an extended planar structure. It is anticipated that the self-ordering of such materials will result in interesting mechanical and electronic properties. Two synthetic strategies for the realisation of macrodiscotic materials are reviewed: firstly, the preparation of molecules which possess a single extended discotic core and secondly, the assembly of rigid, planar macromolecules composed of a random array of fused discotic units. Oxanthrene-based phthalonitrile precursors, prepared by high yielding reactions between catechols and 4,5-dichlorophthalonitrile, are used to explore both strategies for the synthesis of macrodiscotic materials that incorporate phthalocyanine (Pc) as the discotic unit.{Basis of a presentation given at Materials Discussion No. 4,[11][12][13][14]

Macrodiscotic triphenylenophthalocyanines

“…To date the largest macrodiscotic compound based on a phthalocyanine-type structure is the pyrazinoporphyrazine 1. [3][4][5] Synthesis of the parent structure is far more complex and in this paper we report the first heavily substituted triphenylenophthalocyanines 3-5. Non-planar, 'open' structures 2 have been described by Simon and were found to be mesogenic.…”

Porphyrin-based nanoporous network polymers

“…This involves the formation of rigid dibenzodioxane units via an aromatic nucleophilic substitution mechanism (S N Ar). 10 Previously, it has been established that the most distant fluorine atom on each of the four mesopentafluorophenyl groups of 1 (i.e. para to the porphyrin core) is readily substituted by nucleophiles such as amines, thiols or phenolate anions.…”

Investigation on Naphthalene and Its Derivatives‐Based Microporous Organic Hyper‐Cross‐Linked Polymers via Different Methodologies

“…For example, Cooper and co‐workers used bis(chloromethyl)aromatic building blocks to obtain a series of HCLPs with permanent microporous structures and comparable SSAs ranging from 700 to 2000 m 2 g −1 . McKeown and co‐workers synthesized a series of amorphous porous polymers with a greatly enhanced SSA up to 2435 m 2 g −1 from a variety of readily available and inexpensive arene building blocks, opening up a new perspective in synthesizing microporous network polymers with high SSAs even in excess of commercially activated carbons. To further simplify the starting materials, Tan and co‐workers used dimethoxymethane (DMM) as an external cross‐linker (ECL) to combine simple aromatics like benzene or biphenyl with rigid methylene bridges via the anhydrous FeCl 3 ‐catalyzed Friedel–Crafts reaction and gained HCLPs with apparent SSAs up to 1391 m 2 g −1 .…”