For the chocolate layer: Place the chocolate chips and cream in a small bowl. Place over a pan of barely simmering water and stir until the chocolate has melted and the mixture is smooth, about 5 minutes. Spoon the mixture into the bottom of 6 espresso cups. Refrigerate until set, about 20 minutes.
For the jelly layer: Pour 1/2 cup water in a medium bowl. Sprinkle the gelatin on top and set aside for 5 minutes until softened. In a small saucepan, combine another 1/2 cup water, sugar, and espresso powder. Bring to a boil, whisking frequently, until the sugar has dissolved. Pour the espresso mixture over the gelatin and whisk until the gelatin has dissolved. Whisk in the coffee liqueur. Set aside to cool, about 15 minutes. Ladle the gelatin mixture over the chocolate layer. Refrigerate until set, about 1 1/2 hours.
For the whipped cream: In a medium bowl, using an electric hand mixer, beat the cream on medium speed until thick. Add the vanilla and beat until the cream holds stiff peaks.
Let the jellies stand at room temperature for 15 minutes. Dollop with whipped cream and serve.