A Triptycene‐Based Enantiopure Bis(Diazadibenzoanthracene) by a Chirality‐Assisted Synthesis Approach

Abstract

By applying ac hirality-assisted synthesis (CAS) approach enantiopured iaminodibromotriptycenes were converted to rigid chiral helical diazadibenzoanthracenes,w hich show besides pronouncedC otton effectsi nc ircular dichroism spectra higher photoluminescence quantum yields as comparable carbacyclic analogues.F or the enantiopure buildingb locks, ap rotocol was developeda llowing the large scale synthesis without the necessity of separation via HPLC.

A Hexagonal Shape‐Persistent Nanobelt of Elongated Rhombic Symmetry with Orthogonal π‐Planes by a One‐Pot Reaction

“…To synthesize tetraammonium salt 5 (Scheme 1), which is one of the reactants for the nanobelt (Scheme 3), the isomeric mixture of dibromo diamino triptycene 2 a/b [14] was transferred to the corresponding nitro amides 3 a/3 b in 37 % yield by applying one‐pot conditions prior described by MacLachlan and co‐workers (1. Ac 2 O; 2.…”

Two Dimensional Triptycene End‐Capping and Its Influence on the Self‐Assembly of Quinoxalinophenanthrophenazines†

“…[ 15 ] Taking advantage of the beneficial combination of the solubilizing effect and the crystallization behavior, a pyrene‐ fused N ‐heteroacene with eleven rectilinearly annulated aromatic rings and two triptycenyl end‐caps was introduced, [ 17 ] showing a well‐resolved 1 H NMR‐spectrum at 298 K in CDCl 3 while the similar π‐backbone with long dodecyloxy groups led to broad peaks in deuterated oDCB, even at elevated temperatures (373 K). [ 13 ] The general concept of using two triptycene end‐caps to substantially increase solubility [ 18 ] was further applied to hexabenzoovalenes, [ 19‐21 ] benzo‐ and naphtothienobenzothiophenes, [ 22 ] chiral bis(diazadibenzoanthracenes), [ 23 ] indigo dyes, [ 24 ] benzo‐fused perylene oligomers, [ 25 ] thieno‐fused coronene nanoribbons [ 26 ] or a nanobelt based cycloiptycene. [ 27 ] However, when only one triptycene end‐cap is attached to QPPs, precise π‐dimerization occurred in the solid state, mostly independent from further substituents at the backbone.…”

Triptycene End‐Capping as Strategy in Materials Chemistry to Control Crystal Packing and Increase Solubility

“…Recently, a triptycene end‐capped diazadibenzoanthracene T‐DDA was synthesized along with its unsubstituted parent compound as model compounds for the synthesis of enantiopure bis(diazadibenzoanthracene)s (Figure 16 a–c) [47] . The solubility of the latter was very low (0.002 mmol/L in CHCl 3 ) despite the presence of the alkyl chains.…”

“…d–f) Triptycene end‐capped indigo T‐IND 1 and crystal structures of T‐IND 1 ( d O ⋅ ⋅ ⋅ H =2.25 Å, CCDC2022650) and the parent indigo ( d π =3.37 Å, CDCC1563460). g,h) Triptycene end‐capped indigo T‐IND 2 with corresponding crystal structure ( d π =2.69 Å, CDCC2023711) [47–48] …”