8 ounces bittersweet chocolate, roughly chopped into 1/4 and 1/2-inch pieces
Preheat the oven to 350 degrees F. Line two sheet pans with parchment paper.
Sift the whole-wheat flour, baking powder, baking soda and salt into a large bowl. Stir in any larger grains caught in the sifter back into the dry ingredients.
Beat the butter and sugars in the bowl of a stand mixer fitted with the paddle attachment until fully combined, about 2 minutes. Use a spatula to scrape the sides of the bowl. Beat in the eggs one at a time followed by the vanilla extract. Dump the dry ingredients into the wet ingredients and mix on low until just combined, about 30 seconds. Add the chocolate and mix on low speed until incorporated.
Scoop the dough into 2-tablespoon-sized balls, and place them on a sheet pan spacing about 3 inches apart. Bake for 16-20 minutes, rotating halfway through baking, until they are deep brown. Slide the cookies on the parchment onto the counter to cool.
Store the cookies in an airtight container.
For ice cream sandwiches: 2-3 pints of ice cream, slightly softened
Place a single scoop of ice cream on a cookie. Gently press another cookie on top, pushing down the ice cream so it is in an even thickness, about 1 inch. Freeze the ice cream sandwiches.
If you want to halve or quarter them, freeze the ice cream sandwiches before cutting with a serrated knife.