Ion　segregation　is　critically　important　for　achieving　high　ion　conductivity　for　anion　exchange　membranes　(AEMs).　Herein,　a　new　bisphenol　monomer　bearing　ten　electron-rich　phenyl　groups　was　designed　and　polymerized　with　various　amounts　of　electron-deficient　4,4′-dihydroxydiphenylsulfone　and　4,4′-difluorobenzophenone　to　yield　dense　and　selective　reaction　sites　for　chloromethylation　and　quaternization.　As　the　most　challenging　step,　chloromethylation　was　optimized　by　tuning　the　reaction　temperature,　reaction　time,　and　reactant　ratios.　Ion　exchange　capacity,　water　uptake,　anion　conductivity,　mechanical　stability,　and　alkaline　stability　of　the　resulting　AEMs　were　characterized　in　detail.　It　is　found　that　chloromethylation　reaction　needed　to　be　carried　out　at　low　equivalent　of　chloromethylation　agents　to　avoid　undesirable　crosslinking.　The　QA-PAEKS-20　sample　with　an　IEC　of　1.19　mmol·g−1　exhibited　a　Cl–　conductivity　of　11.2　mS·cm−1　and　a　water　uptake　of　30.2%　at　80　°C,　which　are　promising　for　AEM　applications.　©　2019,　Chinese　Chemical　Society　Institute　of　Chemistry,　Chinese　Academy　of　Sciences　Springer-Verlag　GmbH　Germany,　part　of　Springer　Nature.