We sought an alternative strategy and contemplated the use of an organophotocatalyst, in order to avoid toxic, precious, and unsustainable transition metal-based photocatalysts. Simultaneously, we envisaged leveraging continuous flow conditions to efficiently and safely handle O 2 as a simple, abundant, benign terminal oxidant, motivated by numerous reports of gas-liquid organophotocatalytic processes. The rapid uptake of continuous flow processing in synthesis of fine materials and pharmaceuticals is worth noting, as is its innovative marriage with visible light irradiation which has drastically enhanced the efficiency, sustainability and safety of photochemical processes. While TPP and Rose Bengal are among popular organophotocatalyst choices for the activation of alkaloids, they are primarily optimized for N-demethylations of opiates and tropanoids, endocyclic C-H cyanations -toN. or oxidations of benzylic amines. We were particularly drawn to 9,10-dicyanoanthracene (DCA) as utilized by Santamaria and coworkers. Using DCA as a potent photooxidant (E 1/2 [ 1 DCA*/DCA •-] = +1.99 V vs SCE) and air as terminal oxidant, variable amounts of N-formyl side product (2a) were obtained in the Ndemethylation of 1a to give 3a (Scheme 2). Our attempts using modified reaction conditions reaction in batch (conditions: 30 W white LED floodlamp, air bubbling, 6 h) yielded complex reaction mixture (crm) with 2a as a major component (for HPLC profile and spectral output of LED used, see SI). In a tubular coil flow reactor, 2a was still the major product but the reaction profile was significantly cleaner. However, the very poor solubility of DCA in MeCN often led to flow channel blockages and longer reaction times. Thus, a catalyst with enhanced solubility was required. Intuitively, introduction of polar substituents should improve the solubility of compounds in polar aprotic solvents. Nitro-and Sulfonic acid-groups are good choices for aromatic compounds as the synthetic process to access them is straightforward. Glöcklhofer and co-workers reported the synthesis of a dinitro derivative of DCA with improved solubility. Sulfonic acids on the other hand carry the advantage of further derivatization of sulfonyl chlorides. Inspired by the intermediates reported in the synthesis of a water-soluble DCA analogue, we began our catalyst synthesis (Figure ). Anthraquinone-2,6-disulfonic acid 4, commercial or easily synthesized from cheap anthraquinone , was reduced by activated Zn in aq. (NH 4 ) 2 CO 3 to afford anthracene-2,6-disulfonic acid 5 in good (65%) yield after acidic workup and recrystallisation from aq. KCl. Electrophilic bromination of the central ring of 5 gave 6 in high (80%) yield. At this stage, our synthesis deviated from the literature cyanation which digested the crude product (containing CuCN) in conc. HNO 3 and liberated toxic HCN gas. However, both Rosenmund von-Braun and Pd-catalysed cyanations failed to cyanate 6 due to its poor solubility in organic solvents. Literature guided us to an alternative strategy; in an attempt to disrupt the  stacking properties of anthracene disulfonic acids (ADS), Tohnai and coworkers reported their derivatization as organic amine salts. They found amines bearing long chains (i.e. n-heptyl and npentyl ) minimized or prevented-stacking interactions of ADS as observed in their crystal structures. Inspired by these reports, we derivatized 6 to increase its solubility in polar aprotic organic solvents, increasing the success of cyanation. Instead of ammonium salts that would hinder characterization and photocatalytic reaction work-up, we achieved this covalently via sulfonamides. Chlorination of 6 with POCl 3 and subsequent trapping of 7 with secondary amines of various chain lengths gave 9,10-dibromoanthracene-2,6-disulfonamides 8a, 8b and 8c (DBAS) in 87, 90 and 74% yields, respectively. Pleasingly, Rosenmund von-Braun cyanation of 8a, 8b and 8c under microwave-assisted (15 min) or thermal (see Supporting Informatios (SI)) heating afforded 9,10-dicyanoanthracene-2,6disulfonamides 9a, 9b and 9c (DCAS) as brilliant yellow solids in 66%, 89% and 26% yields, respectively. We note that the entire synthesis is carried out on gram scale, without chromatography, with straightforward purification via recrystallisation. Photocatalyst 9b (henceforth referred to as 'DCAS') was progressed to evaluation in reactions since it: i) displayed the highest solubility in MeCN and PhCN solvents consistent with its calculated physical property values suggesting it was the least lipophilic and had the highest topological polar surface area and ii) was obtained in the highest overall yield (42% over 5 steps). DCA and DCAS gave similar UV-vis spectra (Figure , right). Both have absorption maxima ( max ) at 420 nm and 395 nm, suggesting sulfonamides at the 2,6-positions hardly affect the absorptive properties of the dicyanoanthracene core. Emission spectra were similar for 1 DCA* and 1 DCAS*. Further characterization is described subsequently (and see SI).