Core expanded, 21,23-dithiadiacenaphtho[1,2-c]porphyrin interactions with [60]fullerene

Abstract

Saddle-shaped 21,23-dithiadiacenaphtho[1,2-c]porphyrin exhibits binding interaction with [60]fullerene in addition to photon absorption bands extending to 1000 nm.

Dual-Tweezer Behavior of an Octapodal Pyrene Porphyrin-Based System as a Host for Fullerenes

“…In the search for new molecular architectures that act as hosts for fullerenes, researchers have focused on porphyrin-based systems. Although porphyrins are known to interact with fullerenes and cocrystallization adducts have been extensively reported, for a single porphyrin core, this interaction is usually too weak to be observed in solution. ,, Therefore, in order to achieve high affinity constants, the preparation of multiporphyrinic cages is required . Considerable efforts have been devoted to the tailoring of such complex systems to improve the interaction with fullerenes.…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…Variously substituted acenaphthylene-fused dithiaporphyrins were reported by Hogan and Sutherland ( Scheme 304 ). 571 Thiophene building blocks were prepared by using the Hinsberg condensation between dimethyl 2,2′-thiodiacetate and acenaphthoquinone 304.1 to give the diester 304.2 , which was transformed into 304.5a – c in three steps. Condensation of these dicarbinols with pyrrole and the subsequent oxidation by DDQ afforded acenaphthylene-fused dithiaporphyrins, 304.6a – c .…”

“… a Reagents and conditions: (a) (1) NaOMe, THF, (2) MeOH, H 2 SO 4 ; (b) LiAlH 4 , diethyl ether; (c) MnO 2 , DCM; (d) n -BuLi, TMEDA, 304.5a from 1-ethynyl-4-dodecyloxybenzene; 304.5b from 1-bromo-4-dodecyloxybenzene; 304.5c from ethynylbenzene; (e) (1) BF 3 ·Et 2 O, pyrrole, (2) DDQ. …”

Long alkoxy substituted N2S2 porphyrins for liquid crystalline property

“…However, recently Bromby et al reported a series of novel N 2 S 2 porphyrins with meso‐phenyl substituted long alkoxy groups that shows interesting optical and electrical properties and could behave as ambipolar materials for organic electronic devices [ 19–22 ] . However, to the best of our knowledge, there are only one reports of self‐assembled 21,23‐dithiaporphyrin having decyl or dodecyl chains that shows columnar liquid crystalline phases (Figure 2).…”

“…[17] Nowak-Kr ol et al mentioned N 4 systems with 12 long alkyloxy groups showing low melting point and showed that the melting point of octyloxy derivative is 55.1 C that is comparable with the porphyrin 3 (54.5 C) with N 2 S 2 system reported in this article. [18] However, recently Bromby et al reported a series of novel N 2 S 2 porphyrins with meso-phenyl substituted long alkoxy groups that shows interesting optical and electrical properties and could behave as ambipolar materials for organic electronic devices [19][20][21][22] . However, to the best of our knowledge, there are only one reports of selfassembled 21,23-dithiaporphyrin having decyl or dodecyl chains that shows columnar liquid crystalline phases (Figure 2).…”